ライフサイエンスコーパス: imidazo

1 thiazol-5-yl)-8-(1-ethylpropyl)-2,6-dimethyl-imidazo [1,2-b]pyridazine (MTIP) inhibited 125I-sauvagin

2 l-yl)-cyclobutyl]-1-(2-phenyl-quinolin-7-yl)-imidazo [1,5-a]pyrazin-8-ylamine (PQIP), which we show i

3 l-yl)-cyclobutyl]-1-(2-phenyl-quinolin-7-yl)-imidazo [1,5-a]pyrazin-8-ylamine using an in vitro progr

4 lyl) acetylene-5,6-dihydro-5-methyl-6-oxo-4H-imidazo [1,5a] [1,4] benzodiazepine-3-carboxylate)] to a

5 ethyl-8-azido-5,6-dihydro-5-methyl-6-oxo-4H-imidazo(1,5-alpha)(1,4)benzodi azepine-3-carboxylate (Ro

6 K(+) competitive imidazo-1,2alpha-pyridines also bind to the luminal surf

7 3-iodo-1H-pyrrolo[3',2':4,5]imidazo-[1,2-a]pyridines and [1,2-b]pyridazines were pre

8 3-dideoxy-2,3-didehydro-d/l-erythrofuranosyl)imidazo[ 1,2-a]pyridine.

9 2-amino-8-(1'-beta-D-2'-deoxyribofuranosyl)-imidazo[1,2-a]-1,3,5-triazin-4 (8H)-one (dP).

10 2-Amino-8-(1'-beta-D-2'-deoxyribofuranosyl)-imidazo[1,2-a]-1,3,5-triazin-4(8H)-on e (dP) implements

11 2-amino-8-(1'-beta-D-2'-deoxyribofuranosyl)-imidazo[1,2-a]-1,3,5-triazin-4(8H)-on e].

12 -amino-5-nitro-2(1H)-pyridone, and , 2-amino-imidazo[1,2-a]-1,3,5-triazin-4(8H)-one) nucleobase pairs

13 es ZTP opposite its Watson-Crick complement, imidazo[1,2-a]-1,3,5-triazin-4(8H)one (trivially P), lay

14 -amino-5-nitro-2(1H)-pyridone and P, 2-amino-imidazo[1,2-a]-1,3,5-triazin-4(8H)one) that were designe

15 (6-amino-5-nitro-2(1H)-pyridone and 2-amino-imidazo[1,2-a]-1,3,5-triazin-4-(8H)-one).

16 obases and two added nucleobases (2-amino-8H-imidazo[1,2-a][1,3,5]triazin-4-one and 6-amino-5-nitropy

17 imidazole ring with the triazine to provide imidazo[1,2-a][1,3,5]triazines.

18 g in a library of substituted 8,9-dihydro-5H-imidazo[1,2-a][1,4]diazepin-7(6H)-ones has been develope

19 (L(1))Br2] (1) bearing a fused pi-conjugated imidazo[1,2-a][1,8]naphthyridine-based abnormal N-hetero

20 to a large variety of 3,6-di(hetero)arylated imidazo[1,2-a]imidazole derivatives.

21 vel access to functionalizable 6-substituted imidazo[1,2-a]imidazole scaffolds is described.

22 ary of diversified 2,3,6-tri(hetero)arylated imidazo[1,2-a]imidazoles was generated in good yields.

23 (5-[4-(N-methoxyamidino)-phenyl]-furan-2-yl)-imidazo[1,2-a]pyr idine-6-carboxamidine (6) was prepared

24 r to 3,7-dihydro-2-methyl-6-(4-methoxyphenyl)imidazo[1,2-a]pyrazin-3-on e (MCLA), which-has been gene

25 Imidazo[1,2-a]pyrazine and imidazo[2,1-a]isoquinoline we

26 We report the discovery of a series of imidazo[1,2-a]pyrazine derivatives as novel inhibitors o

27 novel BET bromodomain inhibitors based on an imidazo[1,2-a]pyrazine scaffold.

28 covery and optimization of a novel series of imidazo[1,2-a]pyrazine Syk inhibitors.

29 rogram aimed to further optimize a series of imidazo[1,2-a]pyrazines as a novel class of potent and s

30 vaccine adjuvants, we hypothesized that the imidazo[1,2-a]pyrazines, readily accessible via the Groe

31 -3-phenyl-6,7,8,9-tetrahydropyrido[3',2':4,5]imidazo[1,2-a]pyri midin-5-ium chloride (PHIP-M1) as mai

32 midinophenyl)-furan-2-yl]-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridi ne-6-carboxamidine acetate salt (7)

33 A new and extensive set of 4-(6-iodo-H-imidazo[1,2-a]pyridin-2-yl)-N-dimethylbenzeneamine (IMPY

34 thesis and biological studies of 2-hydroxy-3-imidazo[1,2-a]pyridin-3-yl-2-phosphonopropionic acid (3-

35 l hydrochloride and 4-chloro-N-[2-(2-thienyl)imidazo[1,2-a]pyridin-3-yl]]benzamide activated the toni

36 s were sensitive to 4-chloro-N-[2-(2-thienyl)imidazo[1,2-a]pyridin-3-yl]benzamide (DS2).

37 delta subunit, DS2 (4-chloro-N-[2-(2-thienyl)imidazo[1,2-a]pyridin-3-yl]benzamide), increased tonic c

38 novel PET tracers (2-(4-[(11)C]methoxyphenyl)imidazo[1,2-a]pyridin-7-amine 7 ([(11)C]RO6924963), N-[(

39 We report also the synthesis of 10 3-imidazo[1,2-a]pyridin-tetrazolo[1,5-a]quinolines in 28-9

40 nt, 2-(4'-dimethylaminophenyl)-6-(123)I-iodo-imidazo[1,2-a]pyridine ((123)I-IMPY), in adjacent brain

41 Moreover, the biologically interesting imidazo[1,2-a]pyridine (alpidem derivative) has been pre

42 otassium tert-butoxide gave the indeno-fused imidazo[1,2-a]pyridine 24 in 98% yield.

43 library of hybrid molecules incorporating an imidazo[1,2-a]pyridine and an urea moiety as novel solub

44 ling of the heteroaromatic carboxylic acids (imidazo[1,2-a]pyridine and isoxazole) with aryl halides.

45 approach to the synthesis of polychlorinated imidazo[1,2-a]pyridine C-3-erythrofuranosides, a palladi

46 umen, and thus its inhibitors, including the imidazo[1,2-a]pyridine class of K(+)-competitive acid bl

47 ed us to synthesize the structurally similar imidazo[1,2-a]pyridine erythrofuranosyl C-nucleosides.

48 ort the discovery of two diverse lead series imidazo[1,2-a]pyridine ethers (IPE) and squaramides (SQA

49 Replacement of the imidazo[1,2-a]pyridine group of the previously reported

50 nomer of 2,6,7-trichloro-3-(erythrofuranosyl)imidazo[1,2-a]pyridine proved to be the most active memb

51 vileged position in the core scaffold of the imidazo[1,2-a]pyridine ring, which can be modified witho

52 into a novel class of uPA inhibitors with an imidazo[1,2-a]pyridine scaffold.

53 An imidazo[1,2-a]pyridine series of ATX inhibitors was iden

54 By modification of the analogous imidazo[1,2-a]pyridine series, the newly reported leads

55 od for coupling of aryl isocyanates with the imidazo[1,2-a]pyridine system via a pentacyclometalated

56 A biologically promising imidazo[1,2-a]pyridine was successfully synthesized thro

57 3)I-IMPY (6-iodo-2-(4'-dimethylamino-)phenyl-imidazo[1,2-a]pyridine) is a novel radiopharmaceutical t

58 ties of an azaindolizinone derivative, spiro[imidazo[1,2-a]pyridine-3,2-idan]-2(3H)-one (ST101 or ZSE

59 oro-2-(4'-(123)I-iodophenyl)-3-(N,N-diethyl)-imidazo[1,2-a]pyridine-3-acetam ide ((123)I-CLINDE) in n

60 oro-2-(4'-(123)I-iodophenyl)-3-(N,N-diethyl)-imidazo[1,2-a]pyridine-3-acetam ide SPECT ((123)I-CLINDE

61 zed intramolecular aminooxygenation produced imidazo[1,2-a]pyridine-3-carbaldehydes in moderate to go

62 esized from 2-[5-(4-cyanophenyl)-furan-2-yl]-imidazo[1,2-a]pyridine-6-carbonitrile (4a), through the

63 e salt of 2-[5-(4-amidinophenyl)-furan-2-yl]-imidazo[1,2-a]pyridine-6-carboxamidine (8a) was obtained

64 gy, two compounds 2-[4-(dimethylamino)phenyl]imidazo[1,2-a]pyridine-8-ol (1) and N(1),N(1)-dimethyl-N

65 , and, above all, adaptability to synthesize imidazo[1,2-a]pyridine-based drug molecules such as Alpi

66 and shows excellent C-3 regioselectivity of imidazo[1,2-a]pyridine.

67 s also applicable for the selenocyanation of imidazo[1,2-a]pyridine.

68 dines and isoquinolines for the synthesis of imidazo[1,2-a]pyridines and 2-phenylimidazo[2,1-a]isoqui

69 A number of substituted imidazo[1,2-a]pyridines and related analogues were selec

70 hort and efficient route to a broad range of imidazo[1,2-a]pyridines from 2-aminopyridines and acetop

71 or the practical synthesis of functionalized imidazo[1,2-a]pyridines from benzaldehydes, 2-aminopyrid

72 100 degrees C) resulted in the formation of imidazo[1,2-a]pyridines in 40-60% yields.

73 2-Aryl-imidazo[1,2-a]pyridines not capable of ESIPT emit in the

74 rison of the properties of six ESIPT-capable imidazo[1,2-a]pyridines shows the influence of various s

75 on/cycloisomerization of propiolates to form imidazo[1,2-a]pyridines was explored.

76 Direct C-3 arylation of imidazo[1,2-a]pyridines with aryl tosylates and mesylate

77 A library of 3-(trifluoromethyl)imidazo[1,2-a]pyridines with broad functionalities have

78 A library of 3-(thiocyanato)imidazo[1,2-a]pyridines with broad functionalities have

79 idative C(sp(2))-H bond functionalization of imidazo[1,2-a]pyridines with dimethyl sulfoxide as the c

80 3-Substituted imidazo[1,2-a]pyridines, imidazo[1,2-a]pyrimidines, and

81 eteroarene such as thiazoles, thiophenes, or imidazo[1,2-a]pyridines, the intermolecular arylation of

82 ro[2,3-c]pyridines, rather than the expected imidazo[1,2-a]pyridines, were obtained, which were chara

83 1,2,3-trimethyl-8-(pentafluorophenylmethoxy)imidazo[1,2-a]pyridinium iodide (TMPFPIP), a reversible

84 Imidazo[1,2-a]pyridyl N-arylpyridazinones were hybridize

85 O6924963), N-[(11)C]methyl-2-(3-methylphenyl)imidazo[1,2-a]pyrimidin-7-amine 8 ([(11)C]RO6931643), an

86 sis of 2-[3-(4-fluoro-3-pyridin-3-yl-phenyl)-imidazo[1,2-a]pyrimidin-7-yl]-propan -2-ol (1), an oral

87 However, the imidazo[1,2-a]pyrimidine moiety is rapidly metabolized b

88 he present methodology is also applicable to imidazo[1,2-a]pyrimidine, imidazo[2,1-b]thiazole and ben

89 d formation leading to highly functionalized imidazo[1,2-a]pyrimidines in good to excellent yields.

90 The imidazo[1,2-a]pyrimidines were shown to bind somewhat mo

91 3-Substituted imidazo[1,2-a]pyridines, imidazo[1,2-a]pyrimidines, and imidazo[1,2-c]pyrimidine

92 ligand and the cyclized 7- and 8-substituted-imidazo[1,2-a]pyrrolo[2,3-e]pyrazine products in the pre

93 cyclic scaffold, the 1,3,3-trisubstituted 1H-imidazo[1,2-alpha]imidazol-2-one (i.e. structure 3).

94 Other aryl iodides such as 3-iodo-imidazo[1,2-alpha]pyridine were also used for the tandem

95 Inhibition of the gastric H,K-ATPase by the imidazo[1,2-alpha]pyridine, SCH28080, is strictly compet

96 inked pyrrolecarbaldehyde and 2,3-dihydro-1H-imidazo[1,2-alpha]pyridine-4-ylium derivatives were iden

97 2',6-difluoro-5'-[3-(1-hydroxy-1-methylethyl)imidazo[1,2-b][1,2,4]triazin- 7-yl]biphenyl-2-carbonitri

98 -2-ium 6-oxides rearranged to 2,3-dihydro-1H-imidazo[1,2-b]indazoles under mild conditions.

99 methyl-1H-pyrazol-5-yl)-8-(m orpholinomethyl)imidazo[1,2-b]pyridazin-6-amine (LY2784544) and 1H-benzi

100 Imidazo[1,2-b]pyridazine compound, SGI-1776 inhibits Pim

101 Identified from a screen of imidazo[1,2-b]pyridazine compounds, SGI-1776 inhibits Pi

102 ass of picornavirus inhibitors comprising an imidazo[1,2-b]pyridazine nucleus was discovered.

103 of high affinity inhibitors of PIM-1 such as imidazo[1,2-b]pyridazines, pyrazolo[1,5-a]pyrimidines, a

104 A series of imidazo[1,2-b]thiazole derivatives is shown to activate

105 sted by modifying the amide portion of these imidazo[1,2-b]thiazole derivatives.

106 tly at either the C-2 or C-3 position of the imidazo[1,2-b]thiazole ring.

107 Cl(3)- or base-catalyzed conditions to yield imidazo[1,2-c]oxazoles and imidazo[2,1-c][1,4]oxazine he

108 eta-d-erythro-pentofuranosyl)-3-(2-oxopropyl)imidazo[1,2-c]pyr imidin-5(6H)-one residue.

109 eta-d-erythro-pentofuranosyl)-3-(2-oxopropyl)imidazo[1,2-c]pyr imidin-5(6H)-one residues can form in

110 -a]pyridines, imidazo[1,2-a]pyrimidines, and imidazo[1,2-c]pyrimidine were obtained regiospecifically

111 Benzo[4,5]imidazo[1,2-c]quinazoline-6-carbonitriles are prepared i

112 Phenanthro[9',10':4,5]imidazo[1,2-f]phenanthridines are blue-emitters, and the

113 eading to barely known phenanthro[9',10':4,5]imidazo[1,2-f]phenanthridines.

114 ride loss to yield a rearomatized dihydro-1H-imidazo[1,2-f]phenanthridinium derivative.

115 .1 mM, whereas the 2-methyl-8-(phenylmethoxy)imidazo[1,2a]pyridine-3-acetonitrile (SCH 28080)-inhibit

116 ively from its luminal surface by protonated imidazo[1,2alpha]pyridines (e.g., SCH28080).

117 ethyl-8-fluoro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a] [1,4]benzodiazepine-3-carboxylate (Ro 15-

118 ethyl-8-azido-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a] [1,4]benzodiazepine-3-carboxylate (Ro 15-

119 8581 (3-bromo-10-(difluoromethyl)-9H-benzo[f]imidazo[1,5-a][1,2,4]triazolo[1,5-d][1,4] diazepine), a

120 gonist 8-azido-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxy lic acid eth

121 ol-1-ones 2, pyrrolo[1,2-c]imidazoles 3, and imidazo[1,5-a]indoles 4 by a simple one-step procedure.

122 und to be pivotal for the achievement of the imidazo[1,5-a]pyridine derivative as well as its amount

123 An imidazo[1,5-a]pyridine derivative was unexpectedly obtai

124 No traces of imidazo[1,5-a]pyridine derivatives were obtained for p-O

125 The synthesis of imidazo[1,5-a]pyridines through denitrogenative transann

126 s been developed to prepare a novel class of imidazo[1,5-a]pyridines.

127 er utilized in a facile one-pot synthesis of imidazo[1,5-a]pyridines.

128 resulted in the most potent ligand among the imidazo[1,5-a]quinoline derivatives described so far.

129 A series of imidazo[1,5-a]quinoline derivatives was designed and syn

130 ggested neuroprotective properties for these imidazo[1,5-a]quinoline derivatives.

131 on interacting with positions 4 and 5 of the imidazo[1,5-a]quinoline nucleus.

132 of the nitro imidazole carboxylate afforded imidazo[1,5-a]quinoxalin-4-one in three steps and 60% ov

133 gy was developed for the construction of the imidazo[1,5-a]quinoxalin-4-one ring system.

134 A series of imidazo[1,5-a]quinoxaline amides, carbamates, and ureas

135 A series of imidazo[1,5-a]quinoxaline piperazine ureas appended with

136 a pipi* state localized at the 1-(2-pyridyl)-imidazo[1,5-alpha]pyridine (= impy) ligand core, with im

137 and dynamics of [ReCl(CO)3(3-R-1-(2-pyridyl)-imidazo[1,5-alpha]pyridine)] complexes (abbreviated ReGV

138 Analogs within the imidazo[1,5-alpha]quinoxalin-4-one series had substantia

139 A series of imidazo[1,5-alpha]quinoxalin-4-ones and imidazo[1,5-alph

140 Compounds within the imidazo[1,5-alpha]quinoxaline urea series had high affin

141 s of imidazo[1,5-alpha]quinoxalin-4-ones and imidazo[1,5-alpha]quinoxaline ureas containing substitut

142 Analogues of the previously described spiro[imidazo[1,5-c]thiazole-3,3'-indoline]-2',5,7(6H,7aH)-tri

143 (4-(trifluoromethyl)phenyl)-1H-p yrazol-4-yl)imidazo[1,5-f][1,2,4]triazine, in nonhuman primates.

144 tion markcis-3,5-dimethylpiperazine)carbonyl]imidazo[1,5a]quinoline- 3-carboxylate) is another simila

145 (ethyl-8-azido-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5alpha][1,4]benzodi azepine-3-carboxylate) exe

146 3 (ethyl-8-azido-6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5alpha][1,4]benzodiazepine-3 -carboxylate) and

147 -(4-Fluorophenyl)-2.3-dihydro-5-(4-puridinyl)imidazo(2, 1-beta)thiazole dihydrochloride.

148 terbenzimidazole (TB), and 5-(naphthyl[2,3-d]imidazo-2-yl)bibenzimidazole (5NIBB), which differ with

149 ntatives of new zwitterionic borane adducts, imidazo[2',1':3,4][1,4,2]diazaborolo[1,5-a]indolium-11-i

150 l-2-(4-bicyclo[2.2.2]octan-1-ol)-4-propyl-1H-imidazo[2,1 -i]purin-5(4H)-one, is a particularly potent

151 erein we report the discovery of the benzo[a]imidazo[2,1,5-c,d]indolizine motif displaying tunable em

152 ,4':10,5,6]anthra[2,1,9-def]thieno[3',4':4,5]imidazo[2,1-a]isoquino line-1,3,8(2H)-trione, 2-(1-hepty

153 Imidazo[1,2-a]pyrazine and imidazo[2,1-a]isoquinoline were also obtained in good yi

154 synthesis of amino-functionalized benzo[4,5]imidazo[2,1-a]isoquinolines and isoquinolino[3,4-b]quino

155 ed to obtain the first representatives of 7H-imidazo[2,1-a]pyrrolo[3,2-c]isoquinoline and 1H-imidazo[

156 dazo[2,1-a]pyrrolo[3,2-c]isoquinoline and 1H-imidazo[2,1-a]pyrrolo[3,4-c]isoquinoline heterocyclic sk

157 arbital) and direct CITCO [6-(4-chlorophenyl)imidazo[2,1-b]1,3thiazole-5-carbaldehyde O-(3,4-dichloro

158 (trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1, 3]oxazine (PA-824), in which the OCH(2

159 reaction was achieved from 6-(2-aminophenyl)imidazo[2,1-b][1,3,4]thiadiazole derivatives and availab

160 The (S)-2-nitro-6-substituted 6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazines have been extensively explor

161 CAR agonist/ligand CITCO [6-(4-chlorophenyl)imidazo[2,1-b][1,3]thiazole-5-carbaldehyde O-(3,4-dichlo

162 port the identification of 6-(4-chlorophenyl)imidazo[2,1-b][1,3]thiazole-5-carbaldehyde O-(3,4-dichlo

163 uman CAR than is prototype 6-(4-chlorophenyl)imidazo[2,1-b][1,3]thiazole-5-carbaldehyde O-(3,4-dichlo

164 the direct CAR activator, 6-(4-chlorophenyl)imidazo[2,1-b][1,3]thiazole-5-carbaldehyde-O-(3,4-dichlo

165 nzo-p-dioxin (TCDD)], CAR [6-(4-chlorophenyl)imidazo[2,1-b][1,3]thiazole-5-carbaldehyde-O-(3,4-dichlo

166 rded for films of benzo[lmn]thieno[3',4':4,5]imidazo[2,1-b][3,8]phenanthroline-1,3,6(2H)-trione, 2-oc

167 onstruction of a variety of aryl-substituted imidazo[2,1-b]benzothiazoles, -[2,1-b]thiazoles, and -[2

168 fully applied to imidazo[2,1-b]thiazoles and imidazo[2,1-b]benzothiazoles.

169 also applicable to imidazo[1,2-a]pyrimidine, imidazo[2,1-b]thiazole and benzo[d]imidazo[2,1-b]thiazol

170 This methodology is also applicable to imidazo[2,1-b]thiazole and benzo[d]imidazo[2,1-b]thiazol

171 To define the calcium blocker nature of the imidazo[2,1-b]thiazole-1,4-DHPs and their selectivity on

172 the structure-activity relationship of the 4-imidazo[2,1-b]thiazole-1,4-DHPs and to identify which of

173 (vascular and nonvascular) of a series of 4-imidazo[2,1-b]thiazole-1,4-dihydropyridines are reported

174 se to the human CAR ligand 6-(4-chlorophenyl)imidazo[2,1-b]thiazole-5-carbaldehyde O-(3, 4-dichlorobe

175 sence of the CAR activator 6-(4-chlorophenyl)imidazo[2,1-b]thiazole-5-carbaldehyde O-(3,4-dichloroben

176 -piperidin-4-yl)-2-(4-fluoro-phenyl)-benzo[d]imidazo[2,1-b]thiazole-7 -carboxamide), that activated t

177 rimidine, imidazo[2,1-b]thiazole and benzo[d]imidazo[2,1-b]thiazole.

178 icable to imidazo[2,1-b]thiazole and benzo[d]imidazo[2,1-b]thiazole.

179 methodology has been successfully applied to imidazo[2,1-b]thiazoles and imidazo[2,1-b]benzothiazoles

180 d method for the synthesis of functionalized imidazo[2,1-b]thiazoles starting from benzaldehydes, 2-a

181 idazoles as the substrate, the corresponding imidazo[2,1-b]thiazoles were exclusively obtained.

182 nes, benzimidazo [1,2-a]pyrazine, benzo[4,5] imidazo[2,1-b]thiazoles) directly from 2-aminoheteroaren

183 including thiazolo[3,2-a]benzimidazoles and imidazo[2,1-b]thiazoles, is reported.

184 The synthesis of substituted 3-(5-imidazo[2,1-b]thiazolylmethylene)-2-indolinones and anal

185 intermediate of (5R)-(6Z)-6-(5,6-dihydro-8H-imidazo[2,1-c][1,4]oxazin-2-ylmethylene)-7-oxo -4-thia-1

186 nditions to yield imidazo[1,2-c]oxazoles and imidazo[2,1-c][1,4]oxazine heterocycles.

187 a methylidene penem having a 5,6-dihydro-8H-imidazo[2,1-c][1,4]oxazine heterocyclic substituent at t

188 4-methyl-2-phenyl-(8R)-4,5,7,8-tetrahydro-1H-imidazo[2.1-i]p urin-5-one (PSB-11) at the WT A(3)ARs, b

189 4-methyl-2-phenyl-(8R)-4,5,7,8-tetrahydro-1H-imidazo[2.1-i]pur in-5-one (PSB-11) from the A3 receptor

190 We have identified a series of 1H-imidazo-[4,5-c]quinolines as selective allosteric enhanc

191 1H-Imidazo-[4,5-c]quinolines were prepared while investigat

192 dation to (R)-5,6-dihydro-5-(methylamino)-4H-imidazo[4,5,1-ij]quinolin-2(1H) -one [(R)-6], intermedia

193 azoquinoline (R)-5,6-Dihydro-N,N-dimethyl-4H-imidazo[4,5,1-ij]quinolin-5-amine [(R)-3] is a potent do

194 7-tetrahydro-5-methyl-6-(3-methyl-2-butenyl)imidazo[4,5,1-jk][1, 4]-benzodiazepin-2(1H)-thione monoh

195 common heterocyclic base, 4(7)-amino-6(5) H-imidazo[4,5- d]pyridazin-7(4)one, were screened against

196 on of 7,8-dihalo-2,2-dimethyl-2,3-dihydro-1H-imidazo[4,5-b]phenazine derivatives with good to excelle

197 ing N-alkylated benzo[d]imidazol-2(3H)-ones, imidazo[4,5-b]pyridin-2(3H)-ones, imidazo[4,5-c]pyridin-

198 The synthesis and SAR studies of tricyclic imidazo[4,5-b]pyridin-2-ones as human corticotropin-rele

199 affords highly functionalized unsymmetrical imidazo[4,5-b]pyridin-2-ones in just three synthetic ste

200 nthesis of pseudosymmetrically disubstituted imidazo[4,5-b]pyridin-2-ones, 1,4-disubstituted pyrido[2

201 This led to the discovery of 2-(3H-imidazo[4,5-b]pyridin-2-ylthio)-N-(3,4-dimethoxyphenyl)a

202 romo-2-(4-(4-methylpiperazin-1-yl)phenyl)-3H-imidazo[4,5-b]pyridin-7-yl )piperazin-1-yl)methyl)-5-met

203 -(1H-tetrazol-5-yl)biphe nyl-4-yl]methyl]-3H-imidazo[4,5-b]pyridine ((11)C-KR31173) was injected intr

204 n-1-yl)-2-(1,3-dimethyl-1H-pyrazol-4-yl)-3H -imidazo[4,5-b]pyridine (27e), a potent inhibitor of Auro

205 , and 2-[2-(4-methoxypyridin-2-yl)-ethyl]-3H-imidazo[4,5-b]pyridine (BYK191023) was found to have ver

206 DNA binding properties of fused heterocycles imidazo[4,5-b]pyridine (Ip) and hydroxybenzimidazole (Hz

207 arker of PAHs, and 2-amino-1-methyl-6-phenyl-imidazo[4,5-b]pyridine (PhIP), an HCA, were associated w

208 studies led to the development of purine and imidazo[4,5-b]pyridine analogues with high inhibitory po

209 le beta-deoxynucleoside (B), and 9-methyl-1H-imidazo[4,5-b]pyridine beta-deoxynucleoside (Q), were us

210 C2 direct alkynylation of 3H-imidazo[4,5-b]pyridine derivatives is explored for the f

211 putational modeling approach, appropriate C7-imidazo[4,5-b]pyridine derivatization led to the discove

212 e pairs containing nucleoside Q (9-methyl-1H-imidazo[4,5-b]pyridine) but not the analogue Z (4-methyl

213 tive N-pivaloxy-2-amino-1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridine, 1b, and investigated its chemist

214 lo[3,4-b]pyridine, isoxazolo[3,4-b]pyridine, imidazo[4,5-b]pyridine, and pyrazolo[1,5-a]pyrimidines.

215 HCA) carcinogen 2-amino-1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridine, PhIP, is often generated in the

216 small-molecule BRAF inhibitors based on a 1H-imidazo[4,5-b]pyridine-2(3H)-one scaffold (ring A) as th

217 as the starting point led to a new class of imidazo[4,5-b]pyridine-based inhibitors of Aurora kinase

218 Optimization of the imidazo[4,5-b]pyridine-based series of Aurora kinase inh

219 s formed the basis of a design principle for imidazo[4,5-b]pyridine-derived Aurora-A-selective inhibi

220 ghtforward synthesis of various 2-alkynyl-3H-imidazo[4,5-b]pyridines, a valuable scaffold in drug des

221 Eight 2-phenyl-3H-imidazo[4,5-b]quinoline-9-carbonitriles 15 are prepared

222 les 14 in diphenyl ether affords 2-phenyl-3H-imidazo[4,5-b]quinoline-9-carbonitriles 15 in near quant

223 ange of substituents at all positions of the imidazo[4,5-c]pyrazole nucleus.

224 A new synthetic approach to 4-substituted imidazo[4,5-c]pyrazoles is proposed on the basis of the

225 (3H)-ones, imidazo[4,5-b]pyridin-2(3H)-ones, imidazo[4,5-c]pyridin-2(3H)-ones, benzo[d]oxazol-2(3H)-o

226 is and SAR of a series of 4,5,6,7-tetrahydro-imidazo[4,5-c]pyridine P2X7 antagonists are described.

227 l-5-(diphenylacetyl)- 4, 5,6,7-tetrahydro-1H-imidazo[4,5-C]pyridine-6-carboxylic acid (PD 123319, 1 m

228 the identification of new benzimidazole and imidazo[4,5-c]pyridine-fused ring templates, represented

229 s with various 1,2,4-triazines produced both imidazo[4,5-c]pyridines (3-deazapurines) and pyrido[3,2-

230 in-2-yl)pyrimidin-4-amines and ultimately to imidazo[4,5-c]pyridines and isoquinolines.

231 protocols for the selective chlorination of imidazo[4,5-c]pyridines at the C2 and C7 positions were

232 forded methyl substituted 4,5,6,7-tetrahydro-imidazo[4,5-c]pyridines ultimately leading to the identi

233 Imidazo[4,5-c]pyridines were synthesized in three steps

234 ethyl-2-oxo-8-(quinolin-3-yl)-2,3-dihydro-1H-imidazo[4,5-c]quin olin-1-yl]phenyl} propanenitrile (NVP

235 ng with 1-(4-amino-2-((ethylamino)methyl)-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan- 2-ol as a l

236 n) modifications were made in a series of 1H-imidazo[4,5-c]quinolin-4-amine derivatives as allosteric

237 Imiquimod (1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine) is a TLR7 agonist that i

238 dazoquinoline 2-cyclopentyl-4-phenylamino-1H-imidazo[4,5-c]quinoline (DU124183), the pyridinylisoquin

239 t of analogs seem to be the 2-cyclopentyl-1H-imidazo[4,5-c]quinoline derivatives, of which the 4-phen

240 s the design of [1,3,4]thiadiazolo[3',2':1,2]imidazo[4,5-c]quinolines using a Pictet-Spengler reactio

241 ng standard conditions to afford the desired imidazo[4,5-d]-isothiazole nucleosides, usually as cryst

242 tically pure 3,4-dihydro-5H-pyrido[1',2':1,2]imidazo[4,5-d][1,3]diazepin-5-ones which form a new fami

243 (benzylthio)-6-(2-deoxy-beta-D-ribofuranosyl)imidazo[4,5-d]isothiaz ole (5e), which showed moderate i

244 A series of imidazo[4,5-d]isothiazole nucleosides related to the ant

245 The N-6 glycosylated imidazo[4,5-d]isothiazoles also were inactive in antipro

246 The sodium salt glycosylation of the imidazo[4,5-d]isothiazoles proceeded smoothly, giving mi

247 The N-6 glycosylated imidazo[4,5-d]isothiazoles were completely inactive up t

248 The central 5H-imidazo[4,5-d]pyridazine core was formed from acid-catal

249 The 1H-imidazo[4,5-d]pyridazine was identified as scaffold for

250 Here we show that imidazo[4,5-e][1, 4]diazapine nucleotide (I) is a potent

251 a series of analogues (1a-1h) containing the imidazo[4,5-e][1,2,4]triazepine ring system has been syn

252 m (9, 14, 15, 18, 24-26, 28, 31, and 33) and imidazo[4,5-e][1,2,4]triazepine ring systems (30b, 30c,

253 d nucleotide analogues (RENs) containing the imidazo[4,5-e][1,3]diazepine ring system (9, 14, 15, 18,

254 ) (dppz = dipyridophenazine, PIP = 2-(phenyl)imidazo[4,5-f][1,10]phenanthroline) immediately stalls r

255 bipyridyl and PICH(2) is (2-(4-carboxyphenyl)imidazo[4,5-f][1,10]phenanthroline).

256 ining the heterocyclic amine 8-[(3-methyl-3H-imidazo[4,5-f]quinolin-2-yl)amino]-2'-deoxyguanosine add

257 n-1-yl)propyl)-2-(4-(pyridin-4-yl)phenyl)-1H-imidazo[4,5-g ]quinoxalin-6(5H)-one (CTA056), that was d

258 An imidazo[4,5-h]isoquinolin-7,9-dione (1) was identified a

259 This was realized by converting 1 to the imidazo[4,5-h]isoquinolin-9-one (20), resulting in an 18

260 ed on a tripartite A-B-C system featuring an imidazo[4,5]pyridin-2-one group hinge binder.

261 ituted central aromatic core connected to an imidazo[4,5]pyridin-2-one scaffold and a substituted ure

262 methyl-5-quinolinyl)-1-piperazinyl]ethyl}-4H-imidazo[5,1-c][1,4]benzox azine-3-carboxamide (GSK588045

263 [4-(trifluoromethyl)pheny l]-1H-pyrazol-4-yl}imidazo[5,1-f][1,2,4]triazine, [(18)F]PF-05270430 (5).

264 Imidazo[5,1-f][1,2,4]triazinones, as isosteres of purine

265 loped for the synthesis of aroyl-substituted imidazo-/benzimidazo-fused isoquinolines.

266 rnative one-pot protocol for the assembly of imidazo/benzimidazo[2,1-a]isoquinolines in moderate to g

267 delta subunit-containing receptors bind the imidazo-benzodiazepines (BZs) flumazenil and Ro15-4513 w

268 lied to the syntheses of hitherto unreported imidazo-fused benzimidazoquinazolines via a deprotection

269 ed method was developed for the synthesis of imidazo-fused pyrrolopyrazines.

270 regioselective cascade synthesis of N-fused imidazo heterocycles has been developed.

271 osides 6, 7-dichloro-1-(beta-D-ribofuranosyl)imidazo inverted question mark4,5-bquinolin-2-one and 6,

272 one and 6,7-dichloro-3-(beta-D-ribofuranosyl)imidazo inverted question mark4,5-bquinolin-2-one were s

273 ed as the key synthetic intermediates in the imidazo inverted question mark4,5-bquinoline series.

274 c cations is presented, based on the dihydro-imidazo-phenanthridinium framework (DIP), that have affi

275 Since the phenylmethoxy ring of the imidazo-pyridine inhibitors binds to TM1/2, as shown by

276 Replacement of the imidazo ring by a pyrimido or diazepino ring enhanced bi

277 on of [3H]WIN 35,428 binding occurred in the imidazo series with compounds containing one or two Cl o

278 A79 than classic BZDs or BZDs that lack a 3'-imidazo substituent (e.g., midazolam).

279 del of the BZD binding site positions the 3'-imidazo substituent of Ro 15-4513 near gamma(2)A79.

280 id i-BZDs is related to the volume of the 3'-imidazo substituents.

281 The initial imidazo-thiadiazole scaffold was replaced by a 3-methyl-

282 e describe the successful optimization of an imidazo-thiadiazole series of CDK8 inhibitors that was i