1H-benzoindole-3-carboxylic acid | 71692-45-0

• 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
• 英文名称: 1H-benzoindole-3-carboxylic acid
• 英文别名: benzo[g]indole-3-carboxylic acid；1H-benzo[g]indole-3-carboxylic acid；<6.7>Benzindazol-3-carbonsaeure；Benzindole-3-carboxylic acid；1H-benzo[g]indole-3-carboxylic acid
• CAS: 71692-45-0
• 化学式: C₁₃H₉NO₂
• 分子量: 211.22
• InChiKey: PWKSXJWFZTYXJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 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：
  53.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1H-benzoindole-3-carboxylic acid 在 氯化亚砜 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 methyl 1H-benzo[g]indole-3-carboxylate
  参考文献：
  名称：

  Base-Mediated Carboxylation of Unprotected Indole Derivatives with Carbon Dioxide

  摘要：

  A simple and straightforward method for the preparation of indole-3-carboxylic acids was discovered through the direct carboxylation of indoles with atmospheric pressure of carbon dioxide (CO2) under basic conditions. The key for the reaction was found to be the use of a large excess of LiO'Bu as a base to suppress the undesired decarboxylation side reaction.

  DOI：

  10.1021/ol3025082
• 作为产物：
  描述：

  methyl 1H-benzo[g]indole-3-carboxylate 在 sodium hydroxide 、 水 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以60.4%的产率得到1H-benzoindole-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and D2-like binding affinity of 4,5-dihydro-1H-benzo[g]indole-3-carboxamide derivatives as conformationally restricted 5-phenyl-pyrrole-3-carboxamide analogs

  摘要：

  A series of 4,5-dihydro-1H-benzo[g]-indole-3-carboxamide derivatives 2a-g were synthesized as conformationally restricted analogs of the dopamine D-2-like 5-phenylpyrrole-3-carboxamide ligands and evaluated for their affinity for the dopamine D-2-like receptors. In this series, N3-[(1-ethyltetrahydro-1H-2-pyrrolyl)methyl]-4,5-dihydro-1H-benzo[g]indole-3-carboxamide (2a) showed the highest affinity for D-2-like receptors (IC50 = 160 nM). Replacement of the N-(1-ethyl-2-pyrrolidinyl)methyl side chain with a 2-(N,N-diethylamino)ethyl or a 1-benzyl-4-piperidinyl group (2b, 2d) decreased affinity for the D-2-like receptor. The other compounds tested were found to be devoid of D-2-like binding affinity. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(98)00087-1

文献信息

• [EN] 5-LIPOXYGENASE INHIBITORS<br/>[FR] INHIBITEURS DE 5-LIPOXYGÉNASE
  申请人：RANBAXY LAB LTD

  公开号：WO2012014127A1

  公开（公告）日：2012-02-02

  The present invention relates to sulfonamides derivatives as 5-lipoxygenase (5-LO) inhibitors and a process for their synthesis. The present invention also relates to pharmacological compositions containing these sulfonamides derivatives, as well as methods of treating bronchial asthma, chronic obstructive pulmonary disease, rheumatoid arthritis, multiple sclerosis, Type I diabetes, psoriasis, allograft rejection, inflammatory bowel disease, ulcerative colitis, acne, atherosclerosis, cancer, pruritis, allergic rhinitis and other inflammatory and/or autoimmune disorders.

  本发明涉及磺胺类衍生物作为5-脂氧合酶（5-LO）抑制剂以及它们的合成方法。本发明还涉及含有这些磺胺类衍生物的药物组合物，以及治疗支气管哮喘、慢性阻塞性肺疾病、类风湿关节炎、多发性硬化症、I型糖尿病、牛皮癣、移植物排斥反应、炎症性肠病、溃疡性结肠炎、痤疮、动脉粥样硬化、癌症、瘙痒症、过敏性鼻炎和其他炎症和/或自身免疫性疾病的方法。
• [EN] 5-LIPOXYGENASE INHIBITORS<br/>[FR] INHIBITEURS DE LA 5-LIPOXYGÉNASE
  申请人：RANBAXY LAB LTD

  公开号：WO2011161645A1

  公开（公告）日：2011-12-29

  The present invention relates to pyrazole derivatives and to processes for their synthesis as 5 -lipoxygenase (5-LO) inhibitors. The present invention also relates to pharmacological compositions containing these pyrazole derivatives, as well as methods of treating bronchial asthma, chronic obstructive pulmonary disease, rheumatoid arthritis, multiple sclerosis, Type I diabetes, psoriasis, allograft rejection, inflammatory bowel disease, ulcerative colitis, acne, atherosclerosis, cancer, pruritis, allergic rhinitis and other inflammatory and/or autoimmune disorders.

  本发明涉及吡唑衍生物及其合成过程，作为5-脂氧合酶（5-LO）抑制剂。本发明还涉及含有这些吡唑衍生物的药理学组合物，以及治疗支气管哮喘、慢性阻塞性肺病、类风湿性关节炎、多发性硬化症、I型糖尿病、牛皮癣、移植排斥、炎症性肠病、溃疡性结肠炎、痤疮、动脉粥样硬化、癌症、瘙痒、过敏性鼻炎和其他炎症和/或自身免疫性疾病的治疗方法。
• Synthesis and cytotoxicity of bis(benzo[g]indole-3-carboxamides) and related compounds
  作者：Gérard A. Pinna、Maria A. Pirisi、Giuseppe E. Grella、Laura Gherardini、Jean M. Mussinu、Giuseppe Paglietti、Anna M. Ferrari、Giulio Rastelli

  DOI：10.1002/1521-4184(200112)334:11<337::aid-ardp337>3.0.co;2-y

  日期：2001.12

  A series of bis(benzo[g]indoles) bridged by CX‐(CH2)nN(Me)(CH2)n‐CX (X = O, S, H2; n = 2,3) was synthesized as bifunctional antitumor agents and evaluated for cytotoxic activity against diverse human cancer cell lines by the National Cancer Institute. The parent compounds 2a,b exhibited a good level of activity and derivates 2c— g,i,k demonstrated significant inhibitory effects, all with IC50 values

  合成了一系列由 CX-(CH2)nN(Me)(CH2)n-CX (X = O, S, H2; n = 2,3) 桥接的双(苯并[g]吲哚)作为双功能抗肿瘤剂和由美国国家癌症研究所评估对多种人类癌细胞系的细胞毒活性。母体化合物 2a,b 表现出良好的活性水平，衍生物 2c-g,i,k 表现出显着的抑制作用，IC50 值均在低微摩尔范围内。硫代酰胺类似物 2j 的效力较低。有趣的是，在 2a,b 的苯并 [g] 吲哚部分的苯环上引入取代基不会影响活性，唯一的例外是 7,8-二氯衍生物 2h 变得不那么有效。然后在中空纤维细胞试验中测试了该系列的一个成员 2i，以初步评估其体内抗肿瘤活性。对酰胺 2a 和硫代酰胺 2j 进行了分子建模研究，以解释 2j 对 2a 的活性丧失。最后，根据使用 Poly(dA-dT) .. poly(dA-dT) 的粘度测量判断，化合物 2a 表现为典型的 DNA 嵌入剂。
• Weakly coordinating <i>tert</i>-amide assisted Rh(<scp>iii</scp>)-catalyzed C4-cyanation of indoles: application in photophysical studies
  作者：Souradip Sarkar、Aniruddha Biswas、Sarbojit Das、Bortika Sanyal、Rajkumar Sahoo、Rajarshi Samanta

  DOI：10.1039/d3cc03075j

  日期：——

  A rhodium(iii)-catalyzed indole C4-selective cyanation is described using the bench-stable, user-friendly electrophilic cyanation agent N-cyano-N-phenyl-p-toluenesulfonamide (NCTS) as a coupling partner.

  本研究介绍了一种由铑(iii)催化的吲哚 C4 选择性氰化反应，该反应以工作台稳定、使用方便的亲电氰化剂 N-氰基-N-苯基对甲苯磺酰胺 (NCTS) 为偶联剂。
• Lithium tert-Butoxide-Mediated Carboxylation Reactions of Unprotected Indoles and Pyrroles with Carbon Dioxide
  作者：Shū Kobayashi、Woo-Jin Yoo、Thanh V. Q. Nguyen、Montse Guiteras Capdevila

  DOI：10.3987/com-14-s(k)94

  日期：——

  Unprotected indoles and pyrroles were found to undergo base-mediated carboxylation reactions under ambient pressure of carbon dioxide. It was found that this transition metal-free carboxylation reaction proceeded smoothly with the use of a large excess of (LiOBu)-Bu-t.