3-(4-吡啶)吲哚 | 7272-84-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 3-(4-吡啶)吲哚
• 英文名称: 3-(4-pyridyl)indole
• 英文别名: 3-(4-Pyridyl)indol；4-(3-indolyl)-pyridine；3--indol；Rho Kinase Inhibitor III, Rockout；Rockout；3-pyridin-4-yl-1H-indole
• CAS: 7272-84-6
• 化学式: C₁₃H₁₀N₂
• 分子量: 194.236
• InChiKey: LLJRXVHJOJRCSM-UHFFFAOYSA-N

物化性质

• 溶解度：
  可溶于二甲基亚砜、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 储存条件：
  -20°C

制备方法与用途

3-(4-吡啶基)吲哚（Rockout）是一种Rho激酶(ROCK)抑制剂，IC50值为25μM。在伤口愈合试验中，它能够抑制起泡并导致肌动蛋白应力纤维的溶解【1】。

反应信息

• 作为反应物：
  描述：

  3-(4-吡啶)吲哚 在 alkali 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 2-(4-Indol-3-ylidene-4H-pyridin-1-yl)-1-phenyl-ethanone
  参考文献：
  名称：

  碱性介质中4-（3-吲哚基）吡啶盐的去质子化方向

  摘要：

  DOI：

  10.1007/bf00506994
• 作为产物：
  描述：

  3-(4’-哌啶基)-1H-吲哚 在 palladium on activated charcoal 1,1-二苯乙烯 作用下， 以30%的产率得到3-(4-吡啶)吲哚
  参考文献：
  名称：

  Low molecular weight indole fragments as IMPDH inhibitors

  摘要：

  The study of non-oxazole containing indole fragments as inhibitors of inosine monophosphate dehydrogenase (I MPDH) is described. The synthesis and in vitro inhibitory values for IMPDH II are discussed. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.089

文献信息

• Electrosynthesis of Arylpyrroles and -indoles Under S_RN1 Conditions
  作者：M. Chahma、C. Combellas、A. Thiébault

  DOI：10.1055/s-1994-25476

  日期：——

  Arylpyrroles and -indoles are electrosynthesized via a SRN1 type reaction. With pyrrolyl anion, the reaction leads mainly to α-substitution, but β-substitution and disubstitution are also observed. With indolyl anion, the main product corresponds to β-substitution. In both cases, the yield of the main product is higher than 50%.

  芳基吡咯和吲哚通过SRN1类型反应电合成。使用吡咯基阴离子时，反应主要导致α取代，但也观察到β取代和双取代。使用吲哚基阴离子时，主要产物对应于β取代。在这两种情况下，主要产物的产率均超过50%。
• Direct synthesis of 3-arylindoles via annulation of aryl hydroxylamines with alkynes
  作者：Angus A. Lamar、Kenneth M. Nicholas

  DOI：10.1016/j.tet.2009.03.004

  日期：2009.5

  3-Arylindoles are produced in moderate to excellent yields from the reaction between aryl hydroxylamines and alkynes catalyzed by 10 mol % iron(II) phthalocyanine [Fe(Pc)]. Terminal and internal alkynes afford 3-aryl substituted indoles exclusively. Electron-donating and -withdrawing groups are tolerated on the aryl hydroxylamine. A few bioactive indoles are synthesized as well as several new indoles

  由10摩尔％的酞菁铁（II）[Fe（Pc）]催化的芳基羟胺与炔烃之间的反应，可产生中等至极高的产率的3-Arylindoles。末端和内部炔烃仅提供3-芳基取代的吲哚。给电子基团和吸电子基团在芳基羟胺上是可容忍的。使用这一一步分子间环化程序，可以合成一些生物活性吲哚以及几个新的吲哚。
• Aryl and heteroaryl substituted fused pyrrole anti-inflammatory agents
  申请人：Amgen Inc.

  公开号：US20030096819A1

  公开（公告）日：2003-05-22

  The present invention comprises a new class of novel aryl and heteroaryl substituted fused pyrrole compounds useful for the prophylaxis and treatment of diseases or conditions, such as TNF-&agr;, IL-1&bgr; , IL-6 and/or IL-8 mediated diseases, and other maladies, such as pain and diabetes. In particular, the compounds of the invention are useful for the prophylaxis and treatment of diseases or conditions involving inflammation. Accordingly, the invention also comprises pharmaceutical compositions comprising the compounds of the invention, methods for the prophylaxis and treatment of inflammation and other maladies, such as pain and diabetes, using the compounds and compositions of the invention, and intermediates and processes useful for the preparation of compounds of the invention. The subject invention also relates to processes for making such compounds as well as to intermediates useful in such processes.

  本发明涉及一类新型的芳基和杂环芳基取代融合吡咯化合物，用于预防和治疗疾病或病症，例如TNF-α，IL-1β，IL-6和/或IL-8介导的疾病，以及其他疾病，如疼痛和糖尿病。特别地，本发明的化合物用于预防和治疗涉及炎症的疾病或病症。因此，本发明还包括包含本发明的化合物的制药组合物，使用本发明的化合物和组合物预防和治疗炎症和其他疾病或病症的方法，以及用于制备本发明化合物的中间体和过程。本发明还涉及制备这种化合物的过程以及在这些过程中有用的中间体。
• PROPHYLACTIC OR THERAPEUTIC AGENT FOR AXIAL MYOPIA
  申请人：Osaka University

  公开号：EP2319539A1

  公开（公告）日：2011-05-11

  Since high myopia increases the risks of retinal detachment, myopic chorioretinal atrophy, myopic choroidal neovascularization, glaucoma, and cataract, establishment of prophylaxis against the progress of myopia is desired. However, at present, there is no effective prophylaxis or therapy for axial myopia, which is considered to cause high myopia. The present invention, which was completed based on the finding that Rho kinase inhibitors have an inhibitory action on axial length extension, provides a prominently effective prophylactic or therapeutic agent comprising a Rho kinase inhibitor as an active ingredient for axial myopia.

  由于高度近视会增加视网膜脱离、近视性脉络膜视网膜萎缩、近视性脉络膜新生血管、青光眼和白内障的风险，因此人们希望建立预防近视发展的方法。然而，对于被认为会导致高度近视的轴性近视，目前还没有有效的预防或治疗方法。本发明是在发现 Rho 激酶抑制剂对轴向长度延长具有抑制作用的基础上完成的，它提供了一种由 Rho 激酶抑制剂作为有效成分的显著有效的轴向近视预防或治疗剂。
• Rho kinase inhiitors for use in the treatment of neuroblastoma
  申请人：Academisch Medisch Centrum

  公开号：EP2628482A1

  公开（公告）日：2013-08-21

  The invention therefore provides a Rho kinase inhibitor for the treatment of neuroblastoma. Preferably, said Rho kinase inhibitor causes differentiation of neuroblastoma cells. In a preferred embodiment, said Rho kinase inhibitor is selected from the group consisting of (+)-(R)-trans-4-(1-aminoethyl)-N-(4-piridyl)cyclohexanecarboxamide, 4[(1R)-1-aminoethyl]-N-(4-piridyl)benzamide (Fasudil), 1-(1-Hydroxy-5-isoquinolinesulfonyl)homopiperazine] (Hydroxyfasudil), 2-[4-(1H-indazol-5-yl)phenyl]-2-propanamine, N-(3-methoxybenzyl)-4-(4-piridyl)benzamide, 4-[(trans-4-aminocyclohexyl)amino]-2,5-difluorobenzamide, 4-[(trans-4-aminocyclohexyl)amino]-5-chloro-2-fluorobenzamide, 5-(hexahydro-1H-1,4-diazepin-1-ylsulfonyl)isoquinoline, Isoquinolinesulfonamide (K-115), (S)-(+)-2-methyl-1-[(4-methyl-5-isoquinoline)sulfonyl]-homopiperazine (H-1152P), N-(4-Pyridyl)-N'-(2,4,6-trichlorophenyl)urea, Y-27632, Y-39983, and ROCK siRNA or a pharmaceutically acceptable salt thereof.

  因此，本发明提供了一种用于治疗神经母细胞瘤的 Rho 激酶抑制剂。优选地，所述 Rho 激酶抑制剂可导致神经母细胞瘤细胞分化。在一个优选的实施方案中，所述Rho激酶抑制剂选自由(+)-(R)-反式-4-(1-氨基乙基)-N-(4-iridyl)环己甲酰胺、4[(1R)-1-氨基乙基]-N-(4-iridyl)苯甲酰胺（Fasudil）组成的组、1-(1-羟基-5-异喹啉磺酰基)均哌嗪]（羟基法舒地尔），2-[4-(1H-吲唑-5-基)苯基]-2-丙胺，N-(3-甲氧基苄基)-4-(4-嘧啶基)苯甲酰胺，4-[(反式-4-氨基环己基)氨基]-2、4-[(反式-4-氨基环己基)氨基]-2, 5-二氟苯甲酰胺，4-[(反式-4-氨基环己基)氨基]-5-氯-2-氟苯甲酰胺，5-(六氢-1H-1,4-二氮杂卓-1-基磺酰基)异喹啉，异喹啉磺酰胺 (K-115)、(S)-(+)-2-甲基-1-[(4-甲基-5-异喹啉)磺酰基]-高哌嗪 (H-1152P)、N-(4-吡啶基)-N'-(2,4,6-三氯苯基)脲、Y-27632、Y-39983 和 ROCK siRNA 或其药学上可接受的盐。