4-氯-α-[[2-[[[(1,1-二甲基乙氧基)羰基]氨基]脒甲基]苯并[b]-6-噻吩]氧基]-苯乙酸甲酯 | 947590-61-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-氯-α-[[2-[[[(1,1-二甲基乙氧基)羰基]氨基]脒甲基]苯并[b]-6-噻吩]氧基]-苯乙酸甲酯
• 英文名称: Benzeneacetic acid, 4-chloro-A-[[2-[[[(1,1-dimethylethoxy)carbonyl]amino]iminomethyl]benzo[B]thien-6-YL]oxy]-, methyl ester
• 英文别名: methyl 2-(4-chlorophenyl)-2-[[2-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-1-benzothiophen-6-yl]oxy]acetate
• CAS: 947590-61-6
• 化学式: C₂₃H₂₃ClN₂O₅S
• 分子量: 474.965
• InChiKey: NWAVEOBEEFKARI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  6

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	N'-t-Boc-6-hydroxybenzothiophene-2-carboxamidine	947590-65-0	C14H16N2O3S	292.359

反应信息

• 作为反应物：
  描述：

  4-氯-α-[[2-[[[(1,1-二甲基乙氧基)羰基]氨基]脒甲基]苯并[b]-6-噻吩]氧基]-苯乙酸甲酯 、 三氟乙酸 以 二氯甲烷 为溶剂， 生成 (2-carbamimidoylbenzo[b]thiophen-6-yloxy)-2-(4-chlorophenyl)acetic acid methyl ester trifluoroacetate
  参考文献：
  名称：

  Studies of Benzothiophene Template as Potent Factor IXa (FIXa) Inhibitors in Thrombosis

  摘要：

  FIXa is a serine protease enzyme involved in the intrinsic pathway of the coagulation cascade. The upstream intervention of the coagulation cascade in selectively inhibiting FIXa would leave hemostasis Intact via the extrinsic pathway, leading to an optimum combination of efficacy and safety with low incidence of bleeding. We have identified 2-amindinobenzothiophene template as a lead scaffold for FIXa inhibiton based on its homology with urokinase plasminogen activator (uPA). Subsequent SAR work oil the template revealed a number of highly potent FIXa inhibitors, though with moderate selectivity against FXa. X-ray Study with one of the analogues demonstrated active site binding interaction with the induced opening of the S1 beta pocket and a secondary binding at the S2-S4 sites, which is ill direct contrast with the previous finding.

  DOI：

  10.1021/jm901475e
• 作为产物：
  描述：

  N'-t-Boc-6-hydroxybenzothiophene-2-carboxamidine 、 methyl 4-chloromandelate 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 生成 4-氯-α-[[2-[[[(1,1-二甲基乙氧基)羰基]氨基]脒甲基]苯并[b]-6-噻吩]氧基]-苯乙酸甲酯
  参考文献：
  名称：

  Studies of Benzothiophene Template as Potent Factor IXa (FIXa) Inhibitors in Thrombosis

  摘要：

  FIXa is a serine protease enzyme involved in the intrinsic pathway of the coagulation cascade. The upstream intervention of the coagulation cascade in selectively inhibiting FIXa would leave hemostasis Intact via the extrinsic pathway, leading to an optimum combination of efficacy and safety with low incidence of bleeding. We have identified 2-amindinobenzothiophene template as a lead scaffold for FIXa inhibiton based on its homology with urokinase plasminogen activator (uPA). Subsequent SAR work oil the template revealed a number of highly potent FIXa inhibitors, though with moderate selectivity against FXa. X-ray Study with one of the analogues demonstrated active site binding interaction with the induced opening of the S1 beta pocket and a secondary binding at the S2-S4 sites, which is ill direct contrast with the previous finding.

  DOI：

  10.1021/jm901475e

文献信息

• Heterocyclic Compounds and Their Use in the Treatment of Cardiovascular Disease
  申请人：Wang Shouming

  公开号：US20090221564A1

  公开（公告）日：2009-09-03

  Heterocyclic compounds of the formula (I) are provided: wherein ring A, ring B, R 1 , R 2 , R 3 , R 4 , Y, m, n and q are as identified herein. R 1 is in particular amidino. The invention further provides particular benzothiophene compounds. Compounds of the invention may be useful as inhibitors of Factor IXa and in the therapy of cardiovascular conditions and diseases, e.g. thrombosis.

  提供公式（I）的杂环化合物：其中环A、环B、R1、R2、R3、R4、Y、m、n和q如本文所述。 R1特别是氨基亚甲基。该发明还提供特定的苯并噻吩化合物。该发明的化合物可能有助于抑制因子IXa并用于心血管疾病和病症的治疗，例如血栓形成。
• WO2007/96362
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] HETEROCYCLIC COMPOUNDS AND THEIR USE IN THE TREATMENT OF CARDIOVASCULAR DISEASE<br/>[FR] COMPOSES HETEROCYCLIQUES ET LEUR UTILISATION DANS LE TRAITEMENT DES MALADIES CARDIOVASCULAIRES
  申请人：TRIGEN LTD

  公开号：WO2007096362A1

  公开（公告）日：2007-08-30

  [EN] Heterocyclic compounds of the formula (I) are provided: wherein ring A, ring B, R¹, R², R³, R⁴, Y, m, n and q are as defined herein. R1 is in particular amidino. The invention further provides particular benzothiophene compounds. Compounds of the invention may be useful as inhibitors of Factor IXa and in the therapy of cardiovascular conditions and diseases, e.g. thrombosis.
  [FR] La présente invention concerne des composés de formule (I) : le cycle A, le cycle B, R¹, R², R³, R⁴, Y, m, n et q étant tels que définis dans le présent document. R1 est plus particulièrement amidino. La présente invention concerne également des composés particuliers de benzothiophène. Les composés de l'invention peuvent être utiles en tant qu'inhibiteurs du facteur IXa ainsi que dans le traitement de troubles et maladies cardiovasculaires, p. ex. la thrombose.
• Studies of Benzothiophene Template as Potent Factor IXa (FIXa) Inhibitors in Thrombosis
  作者：Shouming Wang、Richard Beck、Toby Blench、Andrew Burd、Stuart Buxton、Maja Malic、Tenagne Ayele、Shaheda Shaikh、Suresh Chahwala、Chaman Chander、Richard Holland、Sandrine Merette、Lihua Zhao、Michael Blackney、Alexandra Watts

  DOI：10.1021/jm901475e

  日期：2010.2.25

  FIXa is a serine protease enzyme involved in the intrinsic pathway of the coagulation cascade. The upstream intervention of the coagulation cascade in selectively inhibiting FIXa would leave hemostasis Intact via the extrinsic pathway, leading to an optimum combination of efficacy and safety with low incidence of bleeding. We have identified 2-amindinobenzothiophene template as a lead scaffold for FIXa inhibiton based on its homology with urokinase plasminogen activator (uPA). Subsequent SAR work oil the template revealed a number of highly potent FIXa inhibitors, though with moderate selectivity against FXa. X-ray Study with one of the analogues demonstrated active site binding interaction with the induced opening of the S1 beta pocket and a secondary binding at the S2-S4 sites, which is ill direct contrast with the previous finding.