2-Benzyl-3-indolecarboxylic acid | 244090-30-0

• 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: 2-Benzyl-3-indolecarboxylic acid
• 英文别名: 2-Benzylindole-3-carboxylic acid；2-benzyl-1H-indole-3-carboxylic acid
• CAS: 244090-30-0
• 化学式: C₁₆H₁₃NO₂
• 分子量: 251.285
• InChiKey: TZOCJQBUJBUDLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  1-苯基丙-1-胺 、 2-Benzyl-3-indolecarboxylic acid 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 1.0h， 以67%的产率得到2-benzyl-N-(1-phenylpropyl)-1H-indole-3-carboxamide
  参考文献：
  名称：

  Replacement of the quinoline system in 2-phenyl-4-quinolinecarboxamide NK-3 receptor antagonists

  摘要：

  Results from a medicinal chemistry approach aimed at replacing the quinoline ring system in the potent and selective human neurokinin-3 (hNK-3) receptor antagonists 1-4 of general formula I are discussed. The data give further insight upon the potential NK-3 pharmacophore. In particular, it is highlighted that both the benzene-condensed ring and the quinoline nitrogen are crucial determinants for optimal binding affinity to the hNK-3 receptor. Some novel compounds maintained part of the binding affinity to the receptor (5, 6, 10 and 13) and compound 5, featuring the naphthalene ring system, appears to be suitable for further modifications; it offers the option to introduce electron-withdrawing groups at position 2 and 4, conferring on the ring an overall electron-deficiency similar to that of the quinoline. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(99)00043-9
• 作为产物：
  描述：

  2-苄基吲哚 在 吡啶 、 水 、 碳酸氢钠 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 2-Benzyl-3-indolecarboxylic acid
  参考文献：
  名称：

  Replacement of the quinoline system in 2-phenyl-4-quinolinecarboxamide NK-3 receptor antagonists

  摘要：

  Results from a medicinal chemistry approach aimed at replacing the quinoline ring system in the potent and selective human neurokinin-3 (hNK-3) receptor antagonists 1-4 of general formula I are discussed. The data give further insight upon the potential NK-3 pharmacophore. In particular, it is highlighted that both the benzene-condensed ring and the quinoline nitrogen are crucial determinants for optimal binding affinity to the hNK-3 receptor. Some novel compounds maintained part of the binding affinity to the receptor (5, 6, 10 and 13) and compound 5, featuring the naphthalene ring system, appears to be suitable for further modifications; it offers the option to introduce electron-withdrawing groups at position 2 and 4, conferring on the ring an overall electron-deficiency similar to that of the quinoline. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(99)00043-9

文献信息

• [EN] OXAZOLO-NAPHTHYL ACIDS AS PLAMINOGEN ACTIVATOR INHIBTOR TYPE-1 (PAI-1) MODULATORS USEFUL IN THE TREATMENT OF THROMBOSIS AND CARDIOVASCULAR DISEASES<br/>[FR] ACIDES D'OXAZOLO-NAPHTHYL UTILISES EN TANT MODULATEURS DE L'INHIBITEUR DE TYPE-1 (PAI-1) DE L'ACTIVATEUR DE PLASMINOGENE UTILES DANS LE TRAITEMENT DE LA THROMBOSE ET DES MALADIES CARDIO-VASCULAIRES
  申请人：WYETH CORP

  公开号：WO2006023865A1

  公开（公告）日：2006-03-02

  The present invention relates to oxazolo-naphthyl acids of the formula (I) and methods of using them to modulate PAI-1 expression and to treat PAI-1 related disorders.

  本发明涉及式(I)的噁唑基萘酸化合物，以及利用它们调节PAI-1表达和治疗与PAI-1相关的疾病的方法。
• ESTERS AND AMIDES AS PLA2 INHIBITORS
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0854863A1

  公开（公告）日：1998-07-29
• NOVEL THERAPEUTIC AGENTS THAT MODULATE 5-HT RECEPTORS
  申请人：Advanced Medicine, Inc.

  公开号：EP1083918A1

  公开（公告）日：2001-03-21
• OXAZOLO-NAPHTHYL ACIDS AS PLASMINOGEN ACTIVATOR INHIBITOR TYPE-1(PAI-1) MODULATORS USEFUL IN THE TREATMENT OF THROMBOSIS AND CARDIOVASCULAR DISEASES
  申请人：Wyeth

  公开号：EP1781645A1

  公开（公告）日：2007-05-09
• [EN] ESTERS AND AMIDES AS PLA2 INHIBITORS<br/>[FR] ESTERS ET AMIDES UTILISES EN TANT QU'INHIBITEURS ANTI-PLA2
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：WO1997003951A1

  公开（公告）日：1997-02-06

  (EN) The present invention relates to a novel fatty acid derivative of formula (I), wherein R1 is acyl group; R2 is acyl(lower)alkyl; R3 is hydrogen, aryl(lower)alkyl, etc.; R4 is acyl(lower)alkyl; and X is -O-, -NH- or formula (II) [wherein R5 is lower alkyl, etc.]; and a pharmaceutically acceptable salt thereof, which is useful as a medicament; the processes for the preparation of said fatty acid derivative or a salt thereof; a pharmaceutical composition comprising said fatty acid derivative or a pharmaceutically acceptable salt thereof; etc.(FR) La présente invention concerne un dérivé d'acide gras représenté par la formule générale (I) dans laquelle R1 est un groupe acyle, R2 est alkyle (inférieur) d'acyle, R3 est hydrogène, alkyle (inférieur) d'aryle, etc., R4 est alkyle (inférieur) d'acyle, et X est -O-, -NH- ou un groupe représenté par la formule particulière (II). Dans cette formule particulière (II), R5 est alkyle inférieur, etc. L'invention concerne également un sel de ce dérivé utile comme médicament et admis en pharmacie, des procédés de préparation du dérivé d'acide gras ou de l'un de ses sels, et enfin une composition pharmaceutique comprenant ce dérivé d'acide gras ou l'un de ses sels admis en pharmacie.