2-(羟甲基)-1-苯并噻吩-5-腈 | 105191-15-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 中文名称: 2-(羟甲基)-1-苯并噻吩-5-腈
• 英文名称: 2-(hydroxymethyl)benzo[b]thiophene-5-carbonitrile
• 英文别名: 2-(Hydroxymethyl)benzothiophen-5-carbonitril；2-hydroxymethylbenzo[b]thiophene-5-carbonitrile；2-(Hydroxymethyl)benzo[b]thiophen-5-carbonitril；2-(Hydroxymethyl)-1-benzothiophene-5-carbonitrile
• CAS: 105191-15-9
• 化学式: C₁₀H₇NOS
• 分子量: 189.238
• InChiKey: TUQCQABNZRVQEX-UHFFFAOYSA-N

物化性质

• 沸点：
  409.3±30.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  72.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(羟甲基)-1-苯并噻吩-5-腈 在 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 为溶剂， 生成 苯并[b]噻吩-5-甲腈,2-甲酰基-
  参考文献：
  名称：

  Design, synthesis and structure–Activity relationships of benzoxazinone-Based factor Xa inhibitors

  摘要：

  A series of benzoxazinone derivatives was designed and synthesized as factor Xa inhibitors. We demonstrated that the naphthyl moiety in the aniline-based compounds I and 2 can be replaced with benzene-fused heterobicycles and biaryls to give factor Xa inhibitors with improved trypsin selectivity. The P4 modifications lead to monoamidines which are moderately active. The benzoxazinones 41-45 are potent against factor Xa, retain the improved trypsin selectivity of the corresponding aniline-based compounds, and show strong antithrombotic effect dose responsively. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(02)00927-7
• 作为产物：
  描述：

  5-氰基-2-氟苯甲醛 在 sodium tetrahydroborate 、 TEA 、 碳酸氢钠 、 calcium iodide 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 生成 2-(羟甲基)-1-苯并噻吩-5-腈
  参考文献：
  名称：

  Design, synthesis and structure–Activity relationships of benzoxazinone-Based factor Xa inhibitors

  摘要：

  A series of benzoxazinone derivatives was designed and synthesized as factor Xa inhibitors. We demonstrated that the naphthyl moiety in the aniline-based compounds I and 2 can be replaced with benzene-fused heterobicycles and biaryls to give factor Xa inhibitors with improved trypsin selectivity. The P4 modifications lead to monoamidines which are moderately active. The benzoxazinones 41-45 are potent against factor Xa, retain the improved trypsin selectivity of the corresponding aniline-based compounds, and show strong antithrombotic effect dose responsively. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(02)00927-7

文献信息

• [EN] AROMATIC AMIDINE DERIVATIVES USEFUL AS SELECTIVE THROMBIN INHIBITORS<br/>[FR] DERIVES D'AMIDINE AROMATIQUE UTILES EN TANT QU'INHIBITEURS SELECTIFS DE LA THROMBINE
  申请人：C & C RESEARCH LABORATORIES

  公开号：WO1997045424A1

  公开（公告）日：1997-12-04

  (EN) The present invention relates to a novel thrombin inhibitor which is effective even when orally administered. More specifically, the present invention relates to an aromatic amidine derivative represented by formula (I) and the salts thereof, which show potent selective inhibitory activity for thrombin in which (a), R, R1, R2, R3, A, W, Y and n are defined as described in the specification.(FR) L'invention concerne un nouvel inhibiteur de la thrombine qui est efficace même lorsqu'il est administré par voie orale. Plus spécifiquement, l'invention concerne un dérivé d'amidine aromatique représenté par la formule (I) et des sels de celle-ci, qui présentent une activité inhibitrice sélective pour la thrombine. Dans ladite formule, (a), R, R1, R2, R3 A, W, Y et n sont définis comme décrits dans la spécification.

  本发明涉及一种新型的抑制凝血酶的药物，即使口服也具有有效性。更具体地说，本发明涉及一种芳香基脒衍生物及其盐，其在(a)、R、R1、R2、R3、A、W、Y和n如规范所述的情况下，对凝血酶具有强有力的选择性抑制活性。
• Design, synthesis and biological activity of amidinobicyclic compounds (derivatives of DX-9065a) as factor Xa inhibitors: SAR study of S1 and aryl binding sites
  作者：Satoshi Komoriya、Naoaki Kanaya、Takayasu Nagahara、Asako Yokoyama、Kazue Inamura、Yukio Yokoyama、Shin-ichi Katakura、Tsuyoshi Hara

  DOI：10.1016/j.bmc.2004.02.032

  日期：2004.5

  Since factor Xa (fXa) plays a pivotal role in the blood coagulation cascade, inhibition of fXa is thought to be an effective treatment for a variety of thrombotic events. (2,)-2-[4-[[(3S)-l-Acetimidoyl-3-pyrrolidinyl]oxy]phenyl]-3-(7-amidino-2-naphthyl)propanoic acid hydrochloride pentahydrate (DX-9065a) was previously found in our laboratory as a novel orally active factor Xa inhibitor. DX-9065a exhibits a strong inhibitory activity toward fXa by occupying the substrate recognition (called SI) sites and aryl binding sites of fXa. Herein we describe conversions of the amidinonaphthalene and the acetimidoylpyrrolidine moieties of DX-9065a. Some compounds showed remarkably increased in vitro anti-factor Xa and PRCT activities compared with those of DX9065a. The most promising compound 38 showed four times the prolongation of APTT against DX-9065a after oral administration to rats. (C) 2004 Elsevier Ltd. All rights reserved.
• Dann, Otto; Char, Helmut; Fleischmann, Paul, Liebigs Annalen der Chemie, 1986, # 3, p. 438 - 455
  作者：Dann, Otto、Char, Helmut、Fleischmann, Paul、Fricke, Helmut

  DOI：——

  日期：——
• Aromatic amidine derivatives and salts thereof
  申请人：DAIICHI PHARMACEUTICAL CO., LTD.

  公开号：EP0540051B1

  公开（公告）日：1996-04-03
• DANN, O.;CHAR, H.;FLEISCHMANN, P.;FRICKE, H., LIEBIGS ANN. CHEM., 1986, N 3, 438-455
  作者：DANN, O.、CHAR, H.、FLEISCHMANN, P.、FRICKE, H.

  DOI：——

  日期：——