(S)-3-(4-amidrazonophenyl)-N-cyclopentyl-N-methyl-2-(5,6,7,8-tetrahydronaphthalene-2-sulfonyl)propionamide

• 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: (S)-3-(4-amidrazonophenyl)-N-cyclopentyl-N-methyl-2-(5,6,7,8-tetrahydronaphthalene-2-sulfonyl)propionamide
• 英文别名: (2S)-3-(4-carbamohydrazonoylphenyl)-N-cyclopentyl-N-methyl-2-(5,6,7,8-tetrahydronaphthalen-2-ylsulfonylamino)propanamide
• 化学式: C₂₆H₃₅N₅O₃S
• 分子量: 497.662
• InChiKey: XROPNBXWSHATDQ-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  139
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  L-4-氰基苯丙氨酸 在 N-甲基吗啉 、 吡啶 、 硫化氢 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 、 乙酰氯 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 生成 (S)-3-(4-amidrazonophenyl)-N-cyclopentyl-N-methyl-2-(5,6,7,8-tetrahydronaphthalene-2-sulfonyl)propionamide
  参考文献：
  名称：

  Fluorobenzamidrazone thrombin inhibitors: Influence of fluorine on enhancing oral absorption

  摘要：

  LB30057 (1) is a selective and efficacious oral thrombin inhibitor. Fluorine-substitution on the phenylene ring of the benzamidrazone portion in both compound 1 and its derivatives gave, in many cases, enhanced oral absorption in rats while maintaining the intrinsic potency and selectivity. Compound 2 demonstrated a 3-fold increase in absorption. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00412-6

文献信息

• Structural Modification of an Orally Active Thrombin Inhibitor, LB30057: Replacement of the D-Pocket-binding Naphthyl Moiety
  作者：Koo Lee、Sang Yeul Hwang、Seongwon Hong、Chang Yong Hong、Chang-Seok Lee、Youseung Shin、Sangsoo Kim、Mikyung Yun、Yung Joon Yoo、Myunggyun Kang、Yeong Soo Oh

  DOI：10.1016/s0968-0896(98)00044-3

  日期：1998.6

  An amidrazonophenylalanine derivative LB30057 (2) was identified as a potent (K-i = 0.38 nM), selective, and orally active thrombin inhibitor. As a continuation of studies into benzamidrazone-based thrombin inhibitors, we have structurally modified compound 2 by replacing the naphthyl group with a variety of hydrophobic moieties. This study led to discovery of several compounds with significantly enhanced potency in thrombin inhibition without sacrificing selectivity against trypsin and oral absorption. The highest activity was obtained with compound 23 (K-i = 0.045 nM). (C) 1998 Elsevier Science Ltd. All rights reserved.
• Fluorobenzamidrazone thrombin inhibitors: Influence of fluorine on enhancing oral absorption
  作者：Koo Lee、Won-Hyuk Jung、Sang Yeul Hwang、Sung-Hack Lee

  DOI：10.1016/s0960-894x(99)00412-6

  日期：1999.9

  LB30057 (1) is a selective and efficacious oral thrombin inhibitor. Fluorine-substitution on the phenylene ring of the benzamidrazone portion in both compound 1 and its derivatives gave, in many cases, enhanced oral absorption in rats while maintaining the intrinsic potency and selectivity. Compound 2 demonstrated a 3-fold increase in absorption. (C) 1999 Elsevier Science Ltd. All rights reserved.