(4R)-4-t-butoxycarbonylamino-5-chloropentanoic acid benzyl ester | 244257-59-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (4R)-4-t-butoxycarbonylamino-5-chloropentanoic acid benzyl ester
• 英文别名: benzyl (4R)-4-t-butoxycarbonylamino-5-chloropentanoate；benzyl (4R)-5-chloro-4-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate
• CAS: 244257-59-8
• 化学式: C₁₇H₂₄ClNO₄
• 分子量: 341.835
• InChiKey: LNCJHDKUEVABGA-CQSZACIVSA-N

物化性质

• 沸点：
  469.4±40.0 °C(Predicted)
• 密度：
  1.145±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R)-4-t-butoxycarbonylamino-5-chloropentanoic acid benzyl ester 在 盐酸 、 乙醇 、 palladium diacetate 、 potassium carbonate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三(邻甲基苯基)磷 、 potassium iodide 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 129.0h， 生成 (4R)-4-[(2-aminoquinoline-6-carbonyl)amino]-5-[5-carbamimidoyl-2-(2-carboxy-2-oxoethyl)phenoxy]pentanoic acid
  参考文献：
  名称：

  Optimization of a coagulation factor VIIa inhibitor found in factor Xa inhibitor library☆

  摘要：

  An inhibitor of the complex of factor Vila and tissue factor (fVIIa/TF), 2-substituted-4-amidinophenylpyruvic acid la, was structurally modified with the aim of increasing its potency and selectivity. The lead compound la was originally found in our factor Xa (fXa) inhibitor library on the basis of structural similarity of the primary binding sites of tVIIa and fXa. The design was based on computational docking studies using the extracted active site of tVIIa. Compound 1j was found to inhibit factor VIIa/TF at nanomolar concentration with improved selectivity versus fXa and thrombin and it preferentially prolonged the clotting time in the TF-dependent extrinsic pathway. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.12.033
• 作为产物：
  描述：

  (4R)-4-t-butoxycarbonylamino-5-(methanesulfonyloxy)pentanoic acid benzyl ester 在 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以8.29 g的产率得到(4R)-4-t-butoxycarbonylamino-5-chloropentanoic acid benzyl ester
  参考文献：
  名称：

  Optimization of a coagulation factor VIIa inhibitor found in factor Xa inhibitor library☆

  摘要：

  An inhibitor of the complex of factor Vila and tissue factor (fVIIa/TF), 2-substituted-4-amidinophenylpyruvic acid la, was structurally modified with the aim of increasing its potency and selectivity. The lead compound la was originally found in our factor Xa (fXa) inhibitor library on the basis of structural similarity of the primary binding sites of tVIIa and fXa. The design was based on computational docking studies using the extracted active site of tVIIa. Compound 1j was found to inhibit factor VIIa/TF at nanomolar concentration with improved selectivity versus fXa and thrombin and it preferentially prolonged the clotting time in the TF-dependent extrinsic pathway. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.12.033

文献信息

• Amidinophenylpyruvic acid derivatives
  申请人：AJINOMOTO CO. INC

  公开号：US20030109547A1

  公开（公告）日：2003-06-12

  An amidinophenylpyruvic acid derivative of the following formula, analogs thereof and pharmaceutically acceptable salts thereof have an excellent antagonistic effect against activated blood coagulation factor VII. 1

  以下是该公式的一种氨基苯丙酸衍生物，其类似物和药学上可接受的盐具有出色的对激活的凝血因子VII的拮抗作用。
• Aminoisoquinoline derivatives
  申请人：Ajinomoto Co., Inc.

  公开号：US06825181B1

  公开（公告）日：2004-11-30

  Aminoisoquinoline derivatives of the following formulae or analogs thereof and pharmaceutically acceptable salts thereof are provided. These compounds have an excellent effect of inhibiting activated blood-coagulation factor X, and they are useful as anticoagulants or agents for preventing or treating thrombi or emboli.

  提供以下公式或其类似物和其药学上可接受的盐的氨基异喹啉衍生物。这些化合物具有出色的抑制活化血凝因子X的效果，它们可用作抗凝剂或预防或治疗血栓或栓塞的药物。
• EP1065200
  申请人：——

  公开号：——

  公开（公告）日：——
• Optimization of a coagulation factor VIIa inhibitor found in factor Xa inhibitor library☆
  作者：Kazuyuki Sagi、Koichi Fujita、Masayuki Sugiki、Mitsuo Takahashi、Shunji Takehana、Kazumi Tashiro、Takashi Kayahara、Masahiro Yamanashi、Yumiko Fukuda、Seiji Oono

  DOI：10.1016/j.bmc.2004.12.033

  日期：2005.3.1

  An inhibitor of the complex of factor Vila and tissue factor (fVIIa/TF), 2-substituted-4-amidinophenylpyruvic acid la, was structurally modified with the aim of increasing its potency and selectivity. The lead compound la was originally found in our factor Xa (fXa) inhibitor library on the basis of structural similarity of the primary binding sites of tVIIa and fXa. The design was based on computational docking studies using the extracted active site of tVIIa. Compound 1j was found to inhibit factor VIIa/TF at nanomolar concentration with improved selectivity versus fXa and thrombin and it preferentially prolonged the clotting time in the TF-dependent extrinsic pathway. (C) 2005 Elsevier Ltd. All rights reserved.