ライフサイエンスコーパス: carboline

1 e upon thermolysis led to the expected delta-carboline.

2 ith norharman, but also with carboline and 5-carboline.

3 l phosphoric acid to give an asymmetric beta-carboline.

4 tion of 1,2,3-trisubstituted tetrahydro-beta-carbolines.

5 esis of a variety of 1,4-disubstituted gamma-carbolines.

6 oxygen-substituted tetrahydrocarbolines and carbolines.

7 elimination to give the corresponding gamma-carbolines.

8 ynurenine and new-to-nature halogenated beta carbolines.

9 that allow specific positive modulation by B-carbolines.

10 route to diversely substituted 1,3-diamino-B-carbolines.

11 ndole 5,5-dioxides instead of the expected y-carbolines.

12 cOH at 200 degrees C leads to 1-hydroxy-beta-carbolines.

13 n employed in a unified approach to all four carbolines.

14 t allow specific positive modulation by beta-carbolines.

15 the directing group than N9 in C1-aryl-beta-carbolines.

16 hich is known as the sulfur analogue of beta-carbolines.

17 eric regulatory site of benzodiazepines/beta-carbolines.

18 e 1-methyl-6-hydroxy-1,2,3,4-tetrahydro-beta-carboline (1), known to be formed at elevated levels in

19 t is itself readily aromatized to give alpha-carboline (1).

20 ed medium linked this activity to 1-acetyl-B-carboline (1-ABC).

21 We also show that 1-ethoxycarbonyl-beta-carboline (1-ECBC), a compound previously shown to inhib

22 tetrahydro-beta-carbolines (tetrahydro-beta-carboline, 1-methyltetrahydro-beta-carboline and pinolin

23 dihydronaphthalene for the synthesis of beta-carboline-1-one derivatives at room temperature.

24 ide range of functionalities, affording beta-carboline-1-one derivatives in good yields.

25 ides with bicycloalkenes, to synthesize beta-carboline-1-one derivatives under mild conditions.

26 onal groups and affords a good yield of beta-carboline-1-one derivatives.

27 Treatment of tetrahydro-beta-carboline-1-thione with 2-bromooct-7-enoyl chloride foll

28 -b]indole (5-methyl-1,2,3,4-tetrahydro-gamma-carboline; 1) binds at murine 5-HT(5A) receptors, prelim

29 n (-TsH) resulting in the formation of delta-carbolines 1a and benzofuro[3,2-b]pyridines 2a, respecti

30 -elimination (-TsH), delivering 3-iodo delta-carbolines 1b and benzofuro[3,2-b]pyridines 2b, respecti

31 model carcinogen N-pivaloyloxy-2-amino-alpha-carboline, 2.

32 a vinylogous Mannich reaction to prepare the carboline 22, which has the absolute stereochemistry at

33 r with the BDZ inverse agonist n-methyl-beta-carboline-3-carboxamide (beta-CC), and a seizure rating

34 ceptor partial inverse agonist N-methyl-beta-carboline-3-carboxamide (FG-7142).

35 enge with the anxiogenic drug, N-methyl-beta-carboline-3-carboxamide (FG-7142; a partial inverse agon

36 te ethyl ester (beta-CCE), and N-methyl-beta-carboline-3-carboxamide (FG7142), but not including any

37 ing GABA(A) tone with FG-7142 (N-methyl-beta-carboline-3-carboxamide) improved DMTP at low but not hi

38 y 1 muM diazepam, 30 mM EtOH, and 1 muM beta-carboline-3-carboxy ethyl ester (but not 1 muM Zn(2+) bl

39 eated with methyl 6,7-dimethoxy-4-ethyl-beta-carboline-3-carboxylate (1 microgram) and simply restrai

40 ure threshold, a beta carboline [methyl-beta-carboline-3-carboxylate (beta-CCM)]-induced model of gen

41 Z agonist, methyl 6,7-dimethoxy-4-ethyl-beta-carboline-3-carboxylate (DMCM; 1 or 10 microM), failed t

42 (EC50 = 75 nM), and dimethoxyl-4-ethyl-beta-carboline-3-carboxylate (IC50 = 60 nM).

43 , whereas methyl-6, 7-dimethoxy-4-ethyl-beta-carboline-3-carboxylate inhibited GABAR currents.

44 zenil, and methyl-6,7-dimethoxy-4 ethyl-beta-carboline-3-carboxylate were inactive.

45 n zinc and methyl-6,7-dimethoxy-4-ethyl-beta-carboline-3-carboxylate, and differences in enhancement

46 S-9895 and methyl-6,7-dimethoxy-4-ethyl-beta-carboline-3-carboxylate, had qualitatively similar effec

47 ainst PTZ, methyl-6,7-dimethoxy-4-ethyl-beta-carboline-3-carboxylate, picrotoxin, and amygdala-kindle

48 with the exception of dimethoxy-4-ethyl-beta-carboline-3-carboxylate, which behaved as a partial inve

49 -carboline methyl-6,7-dimethoxy-4-ethyl-beta-carboline-3-carboxylate.

50 esis of 6-(propyloxy)-4-(methoxymethyl)-beta-carboline-3-carboxylic acid ethyl ester (6-PBC, 24, IC50

51 Tetrahydro-beta-carboline-3-carboxylic acids were active against the hyd

52 ization model studies on the tetrahydro beta-carboline (35).

53 The in vivo characterization of gamma-carboline 39 showed considerable exposure levels and goo

54 l pH yields 1-methyl-1,2,3,4-tetrahydro-beta-carboline-5,6-dione (8) that reacts avidly with free glu

55 lutathionyl-1-methyl-1,2,3,4-tetrahydro-beta-carboline-5,6-dione (9A and 9B).

56 of the y-carbolinones 6 afforded aromatic y-carbolines 8.

57 te carcinogenic metabolites of 2-amino-alpha-carboline (AalphaC), a food-derived heterocyclic amine m

58 ion of Twist1 signaling with Harmine, a beta-carboline alkaloid, improved extracellular matrix deposi

59 n approach has been developed utilizing beta-carboline alkaloids as the directing group.

60 The natural B-carboline alkaloids display similarities with neurotrans

61 A number of tremorogenic beta-carboline alkaloids have been found in common plant-deri

62 Thus, comutagenicity of beta-carboline alkaloids with aromatic amines is shown to occ

63 utagen norharman along with two related beta-carboline alkaloids, carboline, and 5-carboline, which w

64 nthesis of two biologically interesting beta-carboline alkaloids, ZK93423 and abecarnil (ZK112119).

65 structurally related 1,2,3,4-tetrahydro-beta-carbolines also bind at 5-HT(5A) receptors, and (d) that

66 The versatility of beta-carboline amides as directing groups is evidenced by oth

67 We report here beta-carboline amides as intrinsic directing groups for C(sp(

68 The highest content of the beta-carbolines among the traditional raw materials was recor

69 ersal of the behavioural phenotype with beta-carboline, an anxiogenic inverse benzodiazepine receptor

70 mines not only with norharman, but also with carboline and 5-carboline.

71 and 4 led to the formation of dihydro delta-carboline and benzofuro[3,2-b]pyridine intermediates, wh

72 ydro-beta-carboline, 1-methyltetrahydro-beta-carboline and pinoline) were good OH radical scavengers

73 or the synthesis of a diverse class of gamma-carbolines and benzofuro[3,2-c]pyridines using correspon

74 activation toward hydroxymethylation of beta-carbolines and isoquinolines as effective directing grou

75 tabolic conversion products, especially beta-carbolines and isoquinolines, act as neurotoxins that in

76 eaction between substituted 1-formyl-9H-beta-carbolines and terminal alkynes in the presence of catal

77 g with two related beta-carboline alkaloids, carboline, and 5-carboline, which were reported the firs

78 oquinoline, 2-methyl-1,2,3,4-tetrahydro-beta-carboline, and 9-methyl-norharmon, suspected to induce P

79 thridine, quinazoline, phthalazine, and beta-carboline, and electrophiles included acetyl chloride, m

80 individually discuss the AD targets of the B-carbolines, and then we focus on the multitarget strateg

81 These high-affinity tetrahydro-beta-carboline antagonists are able to discriminate among the

82 ced receptor affinity, these tetrahydro-beta-carboline antagonists are useful tools for elucidating t

83 lard reaction could be used to generate beta-carboline antioxidants.

84 -quinolinediols, and 1-methyl-3-carboxy-beta-carboline are described.

85 emGPS-NP, we found that the more active beta-carbolines are all more lipophilic and larger than the l

86 beta-Carbolines are bioactive pyridoindole alkaloids occurrin

87 Additionally, the identification of beta-carbolines as selective enhancers of GABA(A)Rs in OLs ma

88 Additionally, the identification of B-carbolines as selective enhancers of GABA(A)Rs in OLs ma

89 contain a tetrahydro-beta-carboline or beta-carboline backbone, respectively.

90 class of substituted 7,8-dichloro-1-oxo-beta-carbolines based on the distinct structural features of

91 ssays produced two promising compounds; beta-carboline-based (5c) and hybrid (13a).

92 ramolecular cyclization of a tetrahydro-beta-carboline-based dipeptide has been developed to prepare

93 Herein, a beta-carboline-based lead (KMA) was developed through ligand-

94 A series of novel beta-carboline-based N-heterocyclic carbenes was prepared via

95 on at the 2-position of both beta- and gamma-carbolines being optimal for HDAC6 activity and selectiv

96 -butylimines and cyclized to beta- and gamma-carbolines by either copper-catalyzed or thermal process

97 ready incorporation of functionality at the carboline C-4 position in an efficient one-pot protocol.

98 Substitutions to the carboline cap group were well-tolerated with substitutio

99 cal application of an anti-inflammatory beta-carboline compound, perlolyrine, was sufficient to signi

100 only demonstrates that biosynthesis of beta-carboline compounds is rich in unexpected chemistry but

101 The beta-carboline compounds norharman and harman exhibit neuroac

102 bacterial species, produces a family of beta-carboline compounds with anti-inflammatory activity.

103 ory coffee has proved to be a source of beta-carboline compounds.

104 n of structurally related 1-ethoxycarbonyl-B-carboline confirms that it inhibits Yak1 and blocks C. a

105 on, and aromatization as key steps to give a-carbolines containing tosyl functionality at the y-carbo

106 e design, synthesis, and evaluation of gamma-carboline-containing compounds as a new class of small-m

107 e N-acetylcysteine moiety linked to the beta-carboline core through a thioether bond.

108 ramework, 3-tosyl-6,9-dihydro-1,2-benzo[a]-y-carbolines, could be achieved from 3-aryl(tosylamino)met

109 Harmaline, a beta-carboline derivative thought to induce tremor by facilit

110 Harmaline, a beta-carboline derivative, is known to produce tremor through

111 one pot synthesis of biologically relevant y-carboline derivatives 6 and spiro[pyrrolidinone-3,3']ind

112 Library of biologically relevant new beta-carboline derivatives and isolation of its cycloruthenat

113 ic advanced reaction products including beta-carboline derivatives and Strecker aldehyde, alongside m

114 metal-free protocol provided tetrahydro-beta-carboline derivatives atom-efficiently under room temper

115 on of allenamides, providing tetrahydro-beta-carboline derivatives embedded with a C1-vinyl functiona

116 versatile precursor to different fused beta-carboline derivatives via simple synthetic transformatio

117 lar iminoannulation, affording various gamma-carboline derivatives with an additional ring fused acro

118 to determine blood levels of two major beta-carboline derivatives, harmane and harmine.

119 Various 6-methoxytetrahydro-beta-carboline derivatives, namely BEN (6-methoxy-1-phenyl-2,

120 es from alkyne and their conversion to vital carboline derivatives.

121 lso furnished the respective beta- and gamma-carboline derivatives.

122 acologically investigated 37 tetrahydro-beta-carboline derivatives.

123 n achieved for the synthesis of dihydro-beta-carboline derivatives.

124 the stereochemistry of such 1,4-additions to carboline-derived, unsaturated lactams was sensitive to

125 We also observed that B-carbolines differentially enhance GABA responses in olig

126 We also observed that beta-carbolines differentially enhance GABA responses in olig

127 ine core structure were functionalized using carboline-directed delta-C(sp(2))-H alkynylations.

128 achieved via a convergent strategy involving carboline disaccharide 3 and hydroxy enediyne thioacetat

129 These novel beta-carbolines display similar growth inhibitory activity in

130 Homobivalent gamma-carbolines displayed similar structure-activity relation

131 e [3-carbomethoxy-4-ethyl-6,7-dimethoxy-beta-carboline (DMCM)] BZD ligands.

132 e agonist, methyl-6,7-dimethoxy-4-ethyl-beta-carboline (DMCM, 10(-2)M).

133 receptors is blocked by flumazenil and beta-carboline-ethyl ester (beta-CCE).

134 e, we show that harmol, a member of the beta-carbolines family with anti-depressant properties, impro

135 The anxiogenic beta-carboline, FG 7142 (20 mg/kg) significantly increased gl

136 mpounds, which combine in one molecule gamma-carboline fragment of dimebon and phenothiazine core of

137 However, synthesis of the expected y-carboline framework, 3-tosyl-6,9-dihydro-1,2-benzo[a]-y-

138 tetrahydroisoquinolines and tetrahydro-beta-carbolines frequently with 99% ee's.

139 ect pathway to access the benzene fused beta-carboline from 2-(1H-indol-3-ylsulfanyl)-phenylamines an

140 gh one-pot cascade synthesis of dihydro-beta-carbolines from alkyne and their conversion to vital car

141 The synthesis of C1-functionalized beta-carbolines from N-Boc norharman is described.

142 ee method for the synthesis of substituted a-carbolines from secondary Morita-Baylis-Hillman (MBH) ac

143 oxy-beta-carbolines, whereas tetrahydro-beta-carbolines gave oxidative and degradation products.

144 bitory activity of methylene blue (MB) gamma-carbolines (gC) conjugates (MB-gCs) against human erythr

145 ng extract allowed the isolation of the beta-carbolines harmane and harmalan as confirmed by ESMS, (1

146 We therefore propose that the beta-carbolines harmane and harmalan represent active compone

147 The naturally occurring beta-carboline, harmane, has been implicated in various physi

148 tified several alkaloids, including the beta-carboline harmine and the isoquinoline berberine, that a

149 zyl-3-ethoxycarbonyl-1,2,3,4-tetrahydro-beta-carbolines has been synthesized via the Pictet-Spengler

150 A variety of substituted beta- and gamma-carbolines have been prepared in moderate to excellent y

151 A variety of 3-substituted beta- and gamma-carbolines have been synthesized from N-substituted 3-io

152 accomplish this, we developed 3-propoxy-beta-carboline hydrochloride (3-PBC), a mixed agonist-antagon

153 moiety to a carbazole (e.g., 34, 36) or beta-carboline (i.e., 37), result in reduced affinity and/or

154 tophan and 1-carboxy-1-methyltetrahydro-beta-carboline in the active CDS extract.

155 The methodology affords various substituted carbolines in good to excellent yields.

156 ries of heterocycle conjugated B-(tetrahydro)carbolines in good yield and enantioselectivity.

157 l groups and afford the diverse dihydro-beta-carbolines in good yield.

158 pot construction of N-fused benzimidazo-beta-carbolines in good yields.

159 anilines to obtain various substituted alpha-carbolines in moderate to excellent yields.

160 vious literature indicates that certain beta-carbolines including harmane modulate central monoamine

161 of cis-1,2,3-trisubstituted tetrahydro-beta-carbolines into the trans isomers via a potential carboc

162 In contrast, beta-carboline inverse-agonism was unaltered in chimeric rece

163 Kitasetaline is one of the very few beta-carbolines isolated from bacteria.

164 tive formation of monohydroxymethylated beta-carboline/isoquinoline products exclusively.

165 o subunits differ in sensitivity to the beta-carboline methyl-6,7-dimethoxy-4-ethyl-beta-carboline-3-

166 ual differences in seizure threshold, a beta carboline [methyl-beta-carboline-3-carboxylate (beta-CCM

167 Further, intra-DRN administration of a beta-carboline mimicked the effects of IS, because rats treat

168 ove of double-stranded DNA and that its beta-carboline moiety plays a role in the binding through int

169 At room temperature (25 C), dihydro-a-carboline motifs were obtained exclusively through Micha

170 strated by the three-step synthesis of gamma-carboline N-methyl ingenine B.

171 e basis of IC50 and reaction rates (k), beta-carbolines (norharman and harman), and tetrahydro-beta-c

172 The tetrahydro-beta-carboline of strictosidine aglycone is converted into ak

173 be synthetically transformed into 1-aroyl-B-carbolines of pharmacological interest.

174 pengler reaction, which yields either a beta-carboline or a tetrahydroquinoline product from an aroma

175 oid harmine, which contain a tetrahydro-beta-carboline or beta-carboline backbone, respectively.

176 in-4-ones expand the menu of tetrahydro-beta-carboline oxidation products.

177 The tricycle carboline P3 unit was discovered by hypothesis-based des

178 echanism for enzymatic catalysis of the beta-carboline product is proposed from these data.

179 zing the stereoselective synthesis of a beta-carboline product.

180 applied to the synthesis of tetrahydro-gamma-carboline products which, under oxidative conditions, co

181 erization of substituted carbazoles and beta-carbolines, providing entry into seldom explored chemica

182 beta-Carbolines reacted with hydroxyl radicals (OH) affording

183 general synthetic route to prepare all four carboline regioisomers by photostimulated cyclization of

184 onding triazolo-fused isoquinolines and beta-carbolines, respectively, in good yields.

185 omatic functionalized 1-aryl-4-hydroxy-gamma-carbolines resulted.

186 construction of the bridged tetrahydro-beta-carboline ring system 5 has been developed that features

187 (b) that an intact 1,2,3,4-tetrahydro-gamma-carboline ring system seems optimal and an N(2)-(3-(subs

188 (KslA) that generate the characteristic beta-carboline ring system.

189 ondensation that generates a tetrahydro-beta-carboline scaffold characterized by a 3S stereocenter.

190 lowing for rapid diversification of the beta-carboline scaffold in moderate to excellent yields.

191 ructure-activity relationship studies, the B-carboline scaffold was identified as a powerful tool for

192 itors (5a-p), typified by a tetrahydro-gamma-carboline scaffold, characterized by high HDAC6 inhibiti

193 tegy for the synthesis of benzene-fused beta-carboline scaffolds has been developed.

194 oxy allenoates afforded dihydrocarboline and carboline scaffolds with carbon-nitrogen nucleophilic 2-

195 e 3-(2-nitrovinyl)-indole and 1-hydroxy-beta-carboline series were identified to have single-digit mi

196 and synthesized approximately 50 novel beta-carbolines structurally related to harmine.

197 ld stress can be mimicked by anxiogenic beta-carbolines such as FG7142.

198 The obtained B-carboline systems represent a versatile synthetic platfo

199 d the two isomers of 1,2,3,4-tetrahydro-beta-carboline (Tca)9 Modifications in the cyclic template re

200 (norharman and harman), and tetrahydro-beta-carbolines (tetrahydro-beta-carboline, 1-methyltetrahydr

201 conditions to give 6,7,8,9-tetrahydro-alpha-carboline that is itself readily aromatized to give alph

202 a valuable route to 1,2,3,4-tetrahydro-beta-carboline (THBC) and isoquinoline scaffolds found in man

203 ubiquity of 1,1'-disubstituted tetrahydro-B-carboline (THBC) motif in alkaloid natural products, dev

204 A general synthesis of 1-vinyltetrahydro-B-carbolines (THBCs) has been achieved via palladium(0)-ca

205 for the synthesis of 1,2,3,4-tetrahydro-beta-carbolines (THBCs) relying on a ruthenium hydride/Bronst

206 In the case of alpha-carbolines, the S(RN)1 methodology complements previousl

207 first report on the synthesis of spiro-beta-carbolines through a multicatalytic cascade process.

208 ts were designed as hybrid molecules of beta-carboline (topoisomerase inhibition moiety) and bis(hydr

209 both laboratory and clinical studies of beta-carboline toxicities.

210 t cycloaddition strategy for obtaining gamma-carbolines under mild conditions was developed.

211 ituted and 1,1-disubstituted tetrahydro-beta-carbolines undergo sodium periodate oxidative ring expan

212 A one-pot synthesis of alpha-carbolines via a palladium-catalyzed aryl amination foll

213 e preparation of 3-substituted pyridines and carbolines via copper-free, palladium-catalyzed Sonogash

214 ngs on the synthesis of alpha-, beta-, gamma-carbolines via PIFA/BF(3).OEt(2)-mediated intramolecular

215 ulfonamido)aryl)nicotinates along with gamma-carbolines, via nitrene insertion followed by rearrangem

216 cted to the action of high temperature, beta-carboline was not detected.

217 Synthesis of substituted beta-carbolines was accomplished by utilizing the catalytic e

218 One-pot synthesis of 3,4-benzo[c]-B-carbolines was achieved from 2-aryl(tosylamino)methyl-3-

219 up tolerance for C1-phenyl/thienyl/PAHs-beta-carbolines was demonstrated.

220 prepare 1-substituted N-Boc-tetrahydro-beta-carbolines was developed by lithiation followed by elect

221 1-phenyl-substituted 1,2,3,4-tetrahydro-beta-carbolines was investigated via a Hammett study.

222 These and other related beta-carbolines were also examined in five recombinant GABAA

223 icity properties of 6-methoxytetrahydro-beta-carbolines were demonstrated for the first time.

224 the 3-amino ligands 40 and 41, all the beta-carbolines were found to exhibit high binding affinity a

225 beta-Carbolines were scavengers of OH in the three assays and

226 ydroxyl radicals (OH) affording hydroxy-beta-carbolines, whereas tetrahydro-beta-carbolines gave oxid

227 The latter undergoes rearrangement to a beta-carboline, which upon brominative oxidation undergoes fu

228 d beta-carboline alkaloids, carboline, and 5-carboline, which were reported the first time in surface

229 ediated oxidation of THBCs easily afforded B-carbolines, which could be synthetically transformed int

230 1,2,3-trisubstituted 1,2,3,4-tetrahydro-beta-carbolines, while the olefinic mechanism had been ruled

231 he formylation/acylation of indoles and beta-carbolines with (NH(4))(2)S(2)O(8) via direct decarboxyl

232 es occurs regioselectively to form various a-carbolines with a wide substrate scope.

233 of various 1,4-disubstituted tetrahydro-beta-carbolines with excellent stereoselectivity (de, ee up t

234 velop a suite of 10 bio-inspired 1-aryl-beta-carbolines with varying DeltaG(rot), from which a strong

235 both cis- and trans-1,2,3,4-tetrahydro-beta-carbolines, with the trans isomer predominating.