3-Benzyl-5-chlorindol-2-carbonsaeureethylester | 26868-66-6

• 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
• 英文名称: 3-Benzyl-5-chlorindol-2-carbonsaeureethylester
• 英文别名: ethyl 3-benzyl-5-chloro-1H-indole-2-carboxylate
• CAS: 26868-66-6
• 化学式: C₁₈H₁₆ClNO₂
• 分子量: 313.784
• InChiKey: UQGIMDILFXEEFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Benzyl-5-chlorindol-2-carbonsaeureethylester 以100%的产率得到
  参考文献：
  名称：

  INABA S.; AKATSU M.; HIROHASHI T.; YAMAMOTO H., CHEM. AND PHARM. BULL. , 1976, 24, NO 5, 1976-1082

  摘要：

  DOI：
• 作为产物：
  描述：

  1-tert-butyl 2-ethyl 3-benzoyl-5-chloro-1H-indole-1,2-dicarboxylate 在 三乙基硅烷 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以32%的产率得到3-Benzyl-5-chlorindol-2-carbonsaeureethylester
  参考文献：
  名称：

  [EN] SUBSTITUTED INDOLES AND THEIR USE AS NON-NUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITORS
  [FR] INDOLES SUBSTITUÉS ET LEUR UTILISATION EN TANT QU'INHIBITEURS NON-NUCLÉOSIDIQUES DE LA TRANSCRIPTASE INVERSE

  摘要：

  本发明涉及化合物I的配方或其药学上可接受的盐，其中R1是酯、酰胺或杂环；R2是C或N；R3是甲氧基或乙氧基基团、烷基或杂环基团；R4是取代或未取代的苯基或杂环芳基；R5是卤素或腈基。本发明还描述了这些化合物作为非核苷类逆转录酶抑制剂（NNRTIs）用于抑制或治疗HIV感染或艾滋病的用途。

  公开号：

  WO2015044928A1

文献信息

• [EN] BETA-ARRESTIN-BIASED CANNABINOID CB1 RECEPTOR AGONISTS AND METHODS FOR MAKING AND USING THEM<br/>[FR] AGONISTES, BIAISÉS EN FAVEUR DE LA BÊTA-ARRESTINE, DES RÉCEPTEURS CB1 AUX CANNABINOÏDES ET LEURS PROCÉDÉS DE PRODUCTION ET D'UTILISATION
  申请人：UNIV NORTH CAROLINA AT GREENSBORO

  公开号：WO2015195486A1

  公开（公告）日：2015-12-23

  The present invention provides compounds having a CB1 receptor-binding moiety and a directing moiety. In related aspects, the invention provides pharmaceutical compositions containing compounds of the invention, methods for inhibiting a pathway modulated in part by the CB1 receptor activity, and methods for treating a condition or disorder mediated in part by CB1 receptor activity. In certain embodiments, the compounds are compounds of Formula (I). Methods of preparing compounds of Formula (I) are also described. In another aspect, the invention provides methods of identifying a selective agonist of the beta-arrestin pathway over the G-protein pathway.

  本发明提供了具有CB1受体结合基团和导向基团的化合物。在相关方面，该发明提供了含有本发明化合物的药物组合物，用于抑制部分受CB1受体活性调节的途径的方法，以及用于治疗部分受CB1受体活性调节的疾病或疾病的方法。在某些实施例中，这些化合物是Formula（I）的化合物。还描述了制备Formula（I）化合物的方法。在另一个方面，该发明提供了识别β-阻滞蛋白途径选择性激动剂的方法，而不是G蛋白途径的方法。
• Indoles as inhibitors of HIV reverse transcriptase
  申请人：MERCK & CO. INC.

  公开号：EP0530907A1

  公开（公告）日：1993-03-10

  Novel indole compounds inhibit HIV reverse transcriptase, and are useful in the prevention or treatment of infection by HIV and the treatment of AIDS, either as compounds, pharmaceutically acceptable salts, pharmaceutical composition ingredients, whether or not in combination with other antivirals, anti-infectives, immunomodulators, antibiotics or vaccines. Methods of treating AIDS and methods of preventing or treating infection by HIV are also described.

  新型吲哚类化合物可以抑制HIV逆转录酶，并且可用于预防或治疗HIV感染以及治疗艾滋病，无论是作为化合物、药学上可接受的盐、药物组成成分，还是与其他抗病毒药物、抗感染药物、免疫调节剂、抗生素或疫苗组合使用。还描述了治疗艾滋病和预防或治疗HIV感染的方法。
• Reactions of 3-benzylindole-2-carbohydrazides: Synthesis of new 10-Benzyl-1,2-dihydro-1-oxo-1,2,4-triazino[4,5-<i>a</i>]indoles and 3-Benzyl-2-(1,3,4-oxadiazol-2-yl)indoles
  作者：Shambabu Joseph Maddirala、Vidya S. Gokak、Linganagouda D. Basanagoudar

  DOI：10.1002/jhet.5570410102

  日期：2004.1

  triethylorthoformate in a polar solvent like DMF yielded only 10-benzyl-1,2-dihydro-1-oxo-1,2,4-triazino[4,5-a]indoles (5) while (4) on reaction with triethylorthoacetate in DMF yielded both 10-benzyl-4-methyl-1,2-dihydro-1-oxo-1,2,4-triazino[4,5-a]indoles (5) and 3-benzyl-2-(5-methyl-1,3,4-oxadiazol-2-yl)indoles (6) instead of only the triazinoindoles as expected. The oxadiazolylindoles (6) were also synthesized

  3-苄基吲哚-2-碳酰肼（4）与原甲酸三乙酯在极性溶剂（如DMF）中反应仅生成10-苄基-1,2-二氢-1-氧代-1,2,4-三嗪基[4,5- a ]吲哚（5）而（4）在DMF中与原乙酸三乙酯反应生成10-苄基-4-甲基-1,2-二氢-1-氧代-1,2,4-三嗪基[4,5- a ]吲哚（ 5）和3-苄基-2-（5-甲基-1,3,4-恶二唑-2-基）吲哚（6）而不是仅预期的三嗪并吲哚。还通过与过量的原酸酯回流（4）来合成恶二唑基羟吲哚（6）。所形成的化合物的结构通过其分析和光谱数据表征。
• Beta-arrestin-biased cannabinoid CB1 receptor agonists and methods for making and using them
  申请人：The University of North Carolina at Greensboro

  公开号：US10118914B2

  公开（公告）日：2018-11-06

  The present invention provides compounds having a CB1 receptor-binding moiety and a directing moiety. In related aspects, the invention provides pharmaceutical compositions containing compounds of the invention, methods for inhibiting a pathway modulated in part by the CB1 receptor activity, and methods for treating a condition or disorder mediated in part by CB1 receptor activity. In certain embodiments, the compounds are compounds of Formula I. Methods of preparing compounds of Formula I are also described. In another aspect, the invention provides methods of identifying a selective agonist of the beta-arrestin pathway over the G-protein pathway.

  本发明提供了具有 CB1 受体结合分子和指导分子的化合物。在相关方面，本发明提供了含有本发明化合物的药物组合物、抑制部分由 CB1 受体活性调节的通路的方法，以及治疗部分由 CB1 受体活性介导的病症或紊乱的方法。在某些实施方案中，化合物是式 I 的化合物。本发明还描述了制备式 I 化合物的方法。在另一个方面，本发明提供了鉴定β-阿司匹林通路的选择性激动剂而不是G-蛋白通路的方法。
• Structure–Activity Relationship Study of Indole-2-carboxamides Identifies a Potent Allosteric Modulator for the Cannabinoid Receptor <b>1</b> (CB1)
  作者：Mariam M. Mahmoud、Hamed I. Ali、Kwang H. Ahn、Aparna Damaraju、Sushma Samala、Venkata K. Pulipati、Srikanth Kolluru、Debra A. Kendall、Dai Lu

  DOI：10.1021/jm4009828

  日期：2013.10.24

  The cannabinoid CB1 receptor is involved in complex physiological functions. The discovery of CB1 allosteric modulators generates new opportunities for drug discovery targeting the pharmacologically important CB1 receptor. 5-Chloro-3-ethyl-N-(4-(piperidin-1-yl)phenethyl)-1H-indole-2-carboxamide (ORG27569; 1) represents a new class of indole-2-carboxamides that exhibit allostery of CBI. To better understand 0 the SAR, a group of indole-2-carboxamide analogues were synthesized and assessed for allostery of the CB1 receptor. We found that within the structure of indole-2-carboxamides, the presence of the indole ring is preferred for maintaining the modulator's high binding affinity for the allosteric site but not for generating allostery on the orthosteric site. However, the C3 substituents of the indole-2-carboxamides significantly impact the allostery of the ligand. A robust CBI allosteric modulator 5-chloro-N-(4-(dimethylamino)phenethyl)-3-pentyl-1H-indole-2-carboxamide (11j) was identified. It showed an equilibrium dissociation constant (K-B) of 167.3 nM with a markedly high binding cooperativity factor (alpha = 16.55) and potent antagonism of agonist-induced GTP gamma S binding.