ライフサイエンスコーパス: quinazoline

1 oup, and (iii) of a hydrophobic group on the quinazoline.

2 bromo ketones/acetates, yielded high purity quinazolines.

3 er cells to undergo apoptosis in response to quinazolines.

4 nto a nitrogen atom, turning quinolines into quinazolines.

5 ne, and aldehyde for high yield syntheses of quinazolines.

6 ctions for the syntheses of benzoxazoles and quinazolines.

7 esis of a small library of alkyl-substituted quinazolines.

8 These efforts originated from quinazoline 1 and through rational design led to the dev

9 d for the synthesis of highly functionalized quinazoline 1-oxides.

10 same ring) - cinnolines (1,2-benzodiazine), quinazolines (1,3-benzodiazine), phthalazines (2,3-benzo

11 ntain a novel central core (7H-pyrrolo[3,2-f]quinazoline-1,3-diamine), which may significantly expand

12 ing expected 3'-phenyl-1'H-spiro[indene-2,2'-quinazoline]-1,3,4'(3'H)-triones were obtained.

13 azole (1a) with 1H-benzo[d]imidazole (1b) or quinazoline (1c).

14 We found that specific substituents at the quinazoline 2-position prevented AO metabolism and this

15 f appropriate polar functional groups at the quinazoline 2-position, thus separating the F16Bpase inh

16 nge of synthetically valuable derivatives of quinazoline-2,4(1H,3H)-dione, 2H-benzo[e] [1,2,4] thiadi

17 properties make the N(2),N(4)-disubstituted quinazoline-2,4-diamine compound series a suitable platf

18 A series of N(2),N(4)-disubstituted quinazoline-2,4-diamines has been synthesized and tested

19 A series of N(2),N(4)-disubstituted quinazoline-2,4-diamines has been synthesized and tested

20 he identification of N(2),N(4)-disubstituted quinazoline-2,4-diamines with minimum inhibitory concent

21 llowing main TPs: 1-(2-benzoic acid)-(1H,3H)-quinazoline-2,4-dione (BaQD), 1-(2-benzoic acid)-(1H,3H)

22 -2-one (BQM), and 1-(2-benzaldehyde)-(1H,3H)-quinazoline-2,4-dione (BQD) in developing zebrafish (Dan

23 Methyl 9-anilinothiazolo[5,4-f]quinazoline-2-carbimidates 1 (EHT 5372) and 2 (EHT 1610)

24 d nonoxidative coupling of 4-(2-bromoanilino)quinazoline-2-carbonitrile; and (3) a nonoxidative Pd(Ar

25 This study demonstrates the utility of the quinazoline-2-carboxamide scaffold for MMP-13 selective

26 MMP-13 inhibitors were synthesized around a quinazoline-2-carboxamide scaffold to facilitate radiola

27 2,4-dione (BaQD), 1-(2-benzoic acid)-(1H,3H)-quinazoline-2-one (BaQM), 9-aldehyde-acridine, 9-carboxy

28 mazepine, 1-(2-benzaldehyde)-4-hydro-(1H,3H)-quinazoline-2-one (BQM), and 1-(2-benzaldehyde)-(1H,3H)-

29 osition 137, and the acceptor 4-aminobenzo[g]quinazoline-2-one (Cf) in lieu of cytidine22 in the i-mo

30 pirocyclic molecule, spiro[3H-indole-3,2'(1H)quinazoline]-2,4'(1H,3H)dione 8, which was also identifi

31 Quinazoline 23 also displayed efficacy in a murine model

32 dearomatized adduct dihydro-6h derived from quinazoline 2h corroborates the proposed dearomative add

33 tized adducts derived from pyrimidine 2a and quinazoline 2n were isolated and characterized.

34 the synthesis of a series of pyrazolo[1,5-a]quinazoline 3- and/or 8-substituted as 5-deaza analogues

35 to provide access to the core pyrazino[2,1-b]quinazoline-3,6-dione (1) scaffold, which is common to s

36 zoline compound, ethyl 5-aminopyrazolo[1,5-a]quinazoline-3-carboxylate, that specifically inhibits ad

37 lyzed skeletal transformation of benzoylated quinazoline 3b nicely appropriated the developed methodo

38 From modestly potent quinazoline 4, we introduced a 5-aza substitution to mas

39 inoxaline moiety in the lead compound (1) by quinazoline (4a-d), 1,2,4-benzotriazine (12a-18b), and q

40 For the rearrangement of quinazoline 5 to 9, the [1,3]-sigmatropic shift of the t

41 Quinazoline 54 and pyrido[3,4-d]pyrimidine 71 were ident

42 yield from starting materials pyridine 5 and quinazoline 6.

43 tion and ring expansion to quinazolino[4,5-b]quinazoline-6,8-dione 7 rather than, as previously belie

44 Benzo[4,5]imidazo[1,2-c]quinazoline-6-carbonitriles are prepared in high yields

45 xy)-ethoxy}-ethoxy] -ethoxy)-ethoxy}-ethoxy]-quinazoline-6-yl-acrylamide ([(18)F]F-PEG6-IPQA), a radi

46 xy)-ethoxy}-ethoxy]- ethoxy)-ethoxy}-ethoxy]-quinazoline-6-yl-acrylamide) ((18)F-PEG(6)-IPQA) for non

47 es, 2-amino-4-(2'-deoxy-beta-D-ribofuranosyl)quinazoline (7) and 2-amino-6-fluoro-4-(2'-deoxy-beta-D-

48 rivatives of benzo[h]quinoline 6 and benzo[h]quinazoline 7a-e as mixed analogues of archetypal 1,8-bi

49 se proprietary kinase library, 4-benzylamino-quinazoline-8-carboxylic acid amide 1 stood out, with su

50 each case, the nitrogen at position-1 of the quinazoline accepted a hydrogen bond from a backbone NH

51 er doxazosin and terazosin (both piperazinyl quinazolines) affect prostate growth via an alpha1-adren

52 Vasicine, an abundantly available quinazoline alkaloid from the leaves of Adhatoda vasica,

53 l-Vasicine is a quinazoline alkaloid with an electron dense ring and add

54 d guanidines termed "lockamers" (cyclophane, quinazoline, aminopyrimidazolines, aminoimidazolines, az

55 In the 2,5-dimethoxybenzylamino substituted quinazoline analogues, replacement of the N9-CH 3 group

56 -c]quinazolines, as well as an imidazo[1,2-c]quinazoline and 4 pyrrolo[2,1-a]isoquinolines, were obta

57 4]oxazino[4,3-a]quinazoline, quinolino[1,2-a]quinazoline and benzo[b]benzo [4,5]imidazo[1,2-d][1,4]ox

58 The net conversion of potent quinazoline and benztriazine inhibitors to cyanoquinolin

59 From models of SD complexed to quinazoline and benztriazine inhibitors, a new class of

60 of fluorescent nucleosides analogues such as quinazoline and oxophenothiazine that should find broad

61 We have developed potent quinazoline and pyrido-[3,4-d]-pyrimidine small molecule

62 hips (SARs) of substituents on the resultant quinazoline and quinoline ring systems led to the identi

63 , SAR, and in vivo evaluation of a series of quinazoline and quinoline-based AAK1 inhibitors are desc

64 we report the design and synthesis of novel quinazoline and quinoline-based small molecules as poten

65 lectrocatalytic C4-H bond diversification of quinazoline and related electron-deficient N-heterocycle

66 acid as a tool to easily produce a range of quinazoline and substituted aniline derivatives using ad

67 rally related to 2-amino-4-oxo-5-substituted quinazolines and 2-amino-4-oxo-5-substituted pyrrolo[2,

68 ng the synthesis of both established and new quinazolines and also highly substituted anilines includ

69 ornenes with a variety of aryl isoquinoline, quinazoline, and picoline derivatives takes place with s

70 pyrimido[1,6-a]benzimidazole, pyrimido[1,6-a]quinazoline, and pyrimido[1,6-a]benzo[b]6-bora-1,3-diazi

71 cyclic aza-arenes including (iso)quinolines, quinazolines, and quinoxalines by utilizing a strain-rel

72 into synthetically challenging pyrimidines, quinazolines, and triazines, respectively.

73 2, and erbB4 were determined for a series of quinazoline- and pyrido[3,4-d]pyrimidine-based analogues

74 ined for a series of alkynamide analogues of quinazoline- and pyrido[3,4-d]pyrimidine-based compounds

75 Unbiased screening identified triazolo[1,5-c]quinazolines as a new-in-class in vitro and in vivo acti

76 ut screening recently identified substituted quinazolines as potent SMN2 inducers.

77 er the optimized condition, 21 pyrrolo[1,2-c]quinazolines, as well as an imidazo[1,2-c]quinazoline an

78 Various coupling partners and quinazolines, as well as other structurally similar hete

79 ization can be induced by the interaction of quinazolines at the ATP site in the absence of receptor

80 ucture-property relationship studies on this quinazoline ATM kinase inhibitor in order to identify st

81 Herein we describe the optimization of a quinazoline based lead to give 18 (SBI-553), a potent an

82 Previous evidence showed the ability of the quinazoline-based alpha(1)-adrenoreceptor antagonist dox

83 ic threshold of prostate cancer cells to the quinazoline-based alpha1-adrenoceptor antagonist doxazos

84 ntial therapeutic significance in the use of quinazoline-based alpha1-adrenoceptor antagonists (alrea

85 evidence that the apoptotic activity of the quinazoline-based alpha1-adrenoceptor antagonists (doxaz

86 Quinazoline-based alpha1-adrenoceptor antagonists such a

87 Recent evidence suggests that the quinazoline-based alpha1-adrenoceptor antagonists, doxaz

88 tive prostate cancer cells, LNCaP, to either quinazoline-based alpha1-agonist by androgens.

89 cycle perturbation in response to ZD1694, a quinazoline-based antifolate thymidylate synthase inhibi

90 very and initial optimization of a selective quinazoline-based compound series that binds with microm

91 This new class of quinazoline-based compounds provides considerable promis

92 Here, we designed and synthesized novel quinazoline-based compounds that simultaneously and sele

93 FR inhibitors possess a structurally related quinazoline-based core scaffold and were identified as A

94 We have discovered a novel series of quinazoline-based CXCR4 antagonists.

95 streamline PROTAC development and establish quinazoline-based degraders as robust chemical tools to

96 old less potent against wild-type EGFR, than quinazoline-based EGFR inhibitors in vitro.

97 ions that are sensitive to existing covalent quinazoline-based EGFR/HER2 inhibitors, with implication

98 substituted with bulky groups, we developed quinazoline-based imaging tools by fluorescently labelin

99 Tandutinib (MLN518/CT53518) is a novel quinazoline-based inhibitor of the type III receptor tyr

100 es to dacomitinib and afatinib, two covalent quinazoline-based inhibitors of EGFR or HER2, respective

101 The model suggests that with the quinazoline-based inhibitors, the N3 atom is hydrogen-bo

102 lly more effective and better tolerated than quinazoline-based inhibitors.

103 ng ATP concentrations suggest that, like the quinazoline-based kinase inhibitors, the pyrrolotriazine

104 binding functional group was introduced to a quinazoline-based PI3K pharmacophore through an appropri

105 sed chemistry to generate a broad library of quinazoline-based PROTACs capable of recruiting a variet

106 Here, we applied a macrocyclic strategy on a quinazoline-based scaffold as a proof-of-concept study w

107 h led to the development of a class of lead (quinazoline-based) compounds with higher potency than do

108 BGC 945 is a cyclopenta[g]quinazoline-based, thymidylate synthase inhibitor specif

109 tment of NSCLC, gefitinib and erlotinib, are quinazoline-based.

110 The NF-kappaB inhibitor quinazoline blocked p65 nuclear translocation and furthe

111 ds used to generate substituted anilines and quinazolines, both privileged pharmacological structures

112 copper is overcome by 2-(6-benzyl-2-pyridyl)quinazoline (BPQ), providing a chemical-biology tool whi

113 or the direct synthesis of 2,4-disubstituted quinazolines by arene Ru(II)benzhydrazone complex via th

114 hich can be converted into the corresponding quinazolines by replacement of the C3 carbon with a nitr

115 y applied for the unprecedented synthesis of quinazolines by the reaction of 2-aminobenzyl alcohol wi

116 we report the discovery of a novel class of quinazoline carboxamides as dual p70S6k/Akt inhibitors f

117 protonation isomers of the distonic-radical quinazoline cation are independently measured with ethyl

118 chloro-2-(2-furyl)-1, 2, 4-triazolo [1, 5-c] quinazoline (CGS-15943).

119 e describe the optimization of the 2-anilino quinazoline class as antimalarial agents.

120 The quinazoline class was exploited to search for a new tran

121 We demonstrated partial efficacy of a lead quinazoline compound in a mouse model of acute Chagas di

122 Two of the compound classes, a quinazoline compound series and an indole compound, also

123 veral orthogonal approaches showed that this quinazoline compound series targeted the ATP-binding poc

124 24 compounds tested, we have identified one quinazoline compound, ethyl 5-aminopyrazolo[1,5-a]quinaz

125 Here, we report a novel small molecule quinazoline compound, Inh2-B1, which specifically inhibi

126 ructure-activity relationship (SAR) study of quinazoline compounds that serve as inhibitors of GCase.

127 hips (SAR) of a series of (iso)quinoline and quinazoline compounds that were synthesized and screened

128 describe a previously unidentified series of quinazoline compounds with potential against Trypanosoma

129 lded a high selectivity toward ABCG2 for the quinazoline compounds.

130 stal structures of EphB3 in complex with two quinazolines confirmed the covalent linkage between the

131 ing of gene clusters for benzodiazepine- and quinazoline-containing polycyclic alkaloids with a wide

132 group of indole alkaloids which include the quinazoline-containing tryptoquivaline (2) that are capa

133 e synthesis used the 6- and 7-OH groups of a quinazoline core as anchor points to connect lenalidomid

134 tructural class containing a 2-(pyridin-2-yl)quinazoline core has been discovered.

135 ubstitution in the 6- and 7-positions of the quinazoline core structure decreased potency.

136 te that despite chemical modification to the quinazoline core these probes still function as ERBB2 in

137 Extension of the aromatic quinazoline core with fluorophore "arms" through substit

138 rough substitution at the 6- position of the quinazoline core with phenyl, styryl, and phenylbutadien

139 alogs of 1a, containing modifications in the quinazoline core, and in the substituents in positions 2

140 modification to the metabolized site on the quinazoline core.

141 he high in vitro and cellular potency of its quinazoline counterpart, but also displayed improved inh

142 ional analysis dealing with N-methyl-NAHs, a quinazoline derivative (19) was designed as a conformati

143 ptophan derivatives of 1, including a unique quinazoline derivative (9).

144 of the key oxygen atom in the linker of the quinazoline derivative also contributed to the activity

145 In summary, the C5-quinazoline derivative D156844 increases SMN expression

146 Finally, a quinazoline derivative suitable to serve as a photoaffin

147 for the synthesis of various quinoxaline and quinazoline derivatives by employing an earth-abundant m

148 ll arylvinyl (styryl), aryl, and arylethynyl quinazoline derivatives by means of different straightfo

149 directly synthesizing acylated and alkylated quinazoline derivatives by the epoxide ring-opening reac

150 d diverse tetracyclic 5H-benzothiazolo[3,2-a]quinazoline derivatives in moderate to good yields.

151 urvival mechanism, we developed new thiourea quinazoline derivatives that are dual inhibitors of both

152 s of new 6-substituted-4-(3-bromophenylamino)quinazoline derivatives that may function as irreversibl

153 An efficient protocol for the synthesis of quinazoline derivatives through nickel-catalyzed ligand-

154 ro-6H,13H-6,12-[1,2]benzenoquinazolino[3,4-a]quinazoline derivatives was produced in good to high yie

155 inal agents to treat proliferative diseases, quinazoline derivatives were synthesized and evaluated p

156 A series of C5-quinazoline derivatives were tested for their ability to

157 is class of compounds led to a new series of quinazoline derivatives with single-digit nanomolar pote

158 ional studies on an "in-house" collection of quinazoline derivatives, featuring highly steric demandi

159 AR agonists in a group of 2-(3-methoxyphenyl)quinazoline derivatives.

160 SAR optimization campaign around a series of quinazoline derived BRAF(V600E) inhibitors.

161 Previous studies documented that the quinazoline-derived alpha1-adrenoceptor antagonist doxaz

162 Here, we show that BIBW2992, an anilino-quinazoline designed to irreversibly bind EGFR and HER2,

163 Quinolines, isoquinolines, and quinazolines, despite containing latent diene and alkene

164 his profile, and, of these, a difluorophenyl quinazoline (DFPQ) derivative was found to be a selectiv

165 e use of high concentrations of irreversible quinazoline EGFR inhibitors such as PF299804.

166 inhibitors, methotrexate, flavopiridol, and quinazoline ErbB1 inhibitors.

167 Diprotonated pyrimidines, quinoxalines, and quinazolines exhibit an unusual regioelectronic effect t

168 n of an HSP70 enzyme, which yielded an amino-quinazoline fragment that was elaborated to a novel ATP

169 he order of 5-isoquinoline > 8-quinoline = 8-quinazoline > 8-isoquinoline > or = cinnoline approximat

170 2+2+2) modular synthesis of multisubstituted quinazolines has been realized by the direct reaction of

171 A broad spectrum of 2,4-disubstituted quinazolines have been successfully derived (25 examples

172 ynthesis of 2-substituted benzothiazoles and quinazolines in excellent yields.

173 compounds, leading to the green synthesis of quinazolines in water.

174 In SKBR-3 cells, the quinazolines induced the formation of inactive EGFR/ErbB

175 Quinazoline-induced EGFR dimerization was abrogated in v

176 Senexins are potent and selective quinazoline inhibitors of CDK8/19 Mediator kinases.

177 We have used quinazoline inhibitors of the epidermal growth factor re

178 Here we report a novel class of GCase quinazoline inhibitors, obtained in a high throughput sc

179 Structural studies of the quinazoline interaction with the EGFR tyrosine kinase do

180 adical-based method of making functionalized quinazolines is described, which relies on microwave-pro

181 es, and thus, direct C4-functionalization of quinazolines is the most convenient way to materialize n

182 , namely, isoquinolines, benzothiazoles, and quinazolines, is demonstrated by employing isocyanides a

183 access to a wide variety of multisubstituted quinazolines, is reported.

184 potent selective small molecule piperazinyl quinazoline kinase inhibitor of the PDGFR, was identifie

185 late which effectively mimics the well-known quinazoline kinase inhibitor scaffold.

186 Crystal structures of amino-quinazoline ligands bound to the different conformationa

187 p27 protein in A431 cells and abrogated the quinazoline-mediated G(1) arrest.

188 cysteine residue and that our electrophilic quinazolines modulate the function of V-ATPase in cells.

189 Quinazoline moieties and particularly C4-substituted qui

190 tween two highly functionalized pyridine and quinazoline moieties by employing a Pd/Walphos catalytic

191 The structure with CB3717 reveals that the quinazoline moiety binds in similar fashion to the pteri

192 ent screens also identified several new lead quinazoline Mps1 inhibitors, including a low-affinity co

193 illus fumigatus Af293 is a known producer of quinazoline natural products, including the antitumor fu

194 antibody, or NF-kappaB activation inhibitor quinazoline (NF-kappaB-I).

195 rase I (Top1) inhibitors, the pyrazolo[1,5-a]quinazoline nucleus, structurally related to the indenoi

196 nd high proteomic specificity, the described quinazolines offer a powerful set of chemical probes to

197 Consistent with the inhibitory effect of quinazolines on receptor kinase activity, the dimers for

198 as isoquinolines, quinoline, phenanthridine, quinazoline, phthalazine, and beta-carboline, and electr

199 uinolines, 1,8-naphthyridines, quinoxalines, quinazolines, pyrimidines, benzimidazoles, pyrroles and

200 This approach resulted in quinazoline-quinoline derivatives as potent inhibitors o

201 e collection of benzo[5,6][1,4]oxazino[4,3-a]quinazoline, quinolino[1,2-a]quinazoline and benzo[b]ben

202 and indazole cores to afford pyrimidines and quinazolines, respectively.

203 ociated with sensitivity to first generation quinazoline reversible EGFR tyrosine kinase inhibitors (

204 Likewise, similar groups on the quinazoline ring also reduced inhibitory activity.

205 e with the phenyl group perpendicular to the quinazoline ring and positioned in the region of the act

206 ds, which are characterized by an acetylated quinazoline ring connected to a 6-5-5 imidazoindolone ri

207 nist NECA 3 and the 1H-[1,2,4]triazolo[1,5-c]quinazoline ring in antagonist CGS15943 1 overlapped, an

208 of Asn-221 still hydrogen bonds to N3 of the quinazoline ring of CB3717, which must be in the enol fo

209 d compound was essentially coplanar with the quinazoline ring system and occupied a pocket between Ly

210 he phenyl group oriented in the plane of the quinazoline ring system and positioned adjacent to the C

211 inazoline was bound in the ATP site with the quinazoline ring system oriented along the peptide stran

212 5,16-hexahydroazepino[4',5':2,3]indolo[1,2-c]quinazoline ring system that has not previously been syn

213 of biologically active compounds contain the quinazoline ring system.

214 e, [1,2,5]-thiadiazolo[3,4-d]pyrimidine, and quinazoline ring systems and evaluated for their ability

215 Several compounds, including quinazoline ring-containing compounds, have been identif

216 preparation of several replacements for the quinazoline scaffold and report these inhibitors' biolog

217 tivity relationship (SAR) exploration of the quinazoline scaffold represented by BIX01294 (1).

218 For comparison, the quinazoline scaffold was reduced to the significantly sm

219 ine moieties and particularly C4-substituted quinazoline scaffolds are widely distributed in biologic

220 Some of the electrophilic quinazolines selectively and potently inhibited EphB3 bo

221 The quinazoline series exhibited cytotoxicity toward eukaryo

222 Here, we describe the optimization of a quinazoline series of JAK inhibitors and the results of

223 This quinazoline series shows potential for treating Chagas d

224 quinoline compounds target DNA gyrase, while quinazoline series target ATP synthase.

225 tlines identification of novel quinoline and quinazoline series through phenotypic screening of the C

226 um for activity in both the isoquinoline and quinazoline series.

227 hown excellent inhibition of TS and, for the quinazoline, significant promise as clinically useful an

228 ubstitution in the 6- and 7-positions of the quinazoline, so that 32 is not the optimal inhibitor for

229 molar concentrations of AG-1478 and AG-1517, quinazolines specific for inhibition of the EGFR kinase,

230 e rapid assembly of either benzimidazoles or quinazolines starting from aryl- or benzyl-substituted c

231 ossessing combinations of similar phenyl and quinazoline substituents do not show this "supra-additiv

232 developed through modifications of the novel quinazoline template I.

233 those employing a therapeutically validated quinazoline template.

234 oid the formation of a novel pyrido[4,3,2-de]quinazoline tetracycle.

235 We have discovered electrophilic quinazolines that covalently modify a soluble catalytic

236 ehyde oxidase (AO), so we sought to identify quinazolines that were not metabolized by AO.

237 ve method for the synthesis of 2-substituted quinazolines through an oxidative workup step.

238 e synthesis of functionalized diazepines and quinazolines through reorganization of the molecular ske

239 e successive assays, we isolated 2-guanidino-quinazoline (TLN468).

240 and characterized a series of electrophilic quinazolines to target this unique, reactive feature in

241 A quinazoline-type compound called ND-011992 has previousl

242 to the structural similarity of ND-011992 to quinazoline-type inhibitors of respiratory complex I, we

243 ZD1839 ("Iressa"), a quinazoline tyrosine kinase inhibitor selective for the

244 BMS-919373 is a highly functionalized quinazoline under investigation as a selective, potent I

245 thesis of quinolines, 2-aminoquinolines, and quinazolines via biomimetic dehydrogenative condensation

246 the biological activity of the pyrrolo[1,2-c]quinazolines was evaluated against Plasmodium falciparum

247 ophenones, acridinones and quinazolinones or quinazolines was identified and measured by liquid chrom

248 s active compound, a series of 2-substituted quinazolines was synthesized and evaluated in several an

249 , NSC194598, a derivative of indeno[1,2,3-de]quinazoline, was found to be a novel G-quadruplex intera

250 A series of 7,8-dialkylpyrrolo[3,2-f]quinazolines were prepared as inhibitors of dihydrofolat

251 uded in the reaction mixture, fully aromatic quinazolines were produced in high yields by a rapid and

252 bstituted quinolines, 2-aminoquinolines, and quinazolines were synthesized in moderate to good yields

253 y acylation of 6-amino-4-(3-bromophenylamino)quinazoline with unsaturated acid chlorides or mixed anh

254 etal-free approach to access pyrazolo-[1,5-c]quinazolines with 3-ylideneoxindoles and tosyldiazometha

255 This study led to the identification of quinazolines with EC50 values in the single digit microm