N-[(3S)-N-(Boc-S-(p-methylbenzyl)-L-cysteinyl)-1,2,3,4-tetrahydroisoquinoline-3-carbonyl]-S-(p-methylbenzyl)-L-cysteine benzyl ester | 1219835-37-6

• 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: N-[(3S)-N-(Boc-S-(p-methylbenzyl)-L-cysteinyl)-1,2,3,4-tetrahydroisoquinoline-3-carbonyl]-S-(p-methylbenzyl)-L-cysteine benzyl ester
• CAS: 1219835-37-6
• 化学式: C₄₄H₅₁N₃O₆S₂
• 分子量: 782.037
• InChiKey: QZQKLBPXCOGILY-IGMOWHQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.55
• 重原子数：
  55.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  114.04
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N-[(3S)-N-(Boc-S-(p-methylbenzyl)-L-cysteinyl)-1,2,3,4-tetrahydroisoquinoline-3-carbonyl]-S-(p-methylbenzyl)-L-cysteine benzyl ester 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 20.0h， 以91%的产率得到N-((3S)-N-(Boc-L-cysteinyl)-1,2,3,4-tetrahydroisoquinoline-3-carbonyl)-L-cysteine
  参考文献：
  名称：

  2,3-Diamino acid modifying 3S-tetrahydroisoquinoline-3-carboxylic acids: Leading to a class of novel agents with highly unfolded conformation, selective in vitro anti-platelet aggregation and potent in vivo anti-thrombotic activity

  摘要：

  In the preparation of anti-thrombotic agents the 2- and 3-positions of 3S-tetra-hydroisoquinoline-3-carboxylic acid (THIQA) were simultaneously modified with amino acids to form 20 novel N-(3S-N-amino-acyl-1,2,3,4-tetrahydroisoquinoline-3-carbonyl) amino acids (8a-t). On an in vitro platelet aggregation model 8a-t selectively inhibit ADP-induced platelet aggregation and their IC50 values are leas than 3.5 nM. On an extracorporeal circulation of arterioveinos cannula model of rats both orally and intraveously effective doses of 8a-t are less than 30 nmol/kg. Cerius(2) based stereoview of explores 8a-t having highly unfolded conformation. 3D QSAR analysis gives the importance of the unfolded conformation to high in vitro anti-platelet aggregation and in vivo anti-thrombotic potency rational understanding. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.01.009
• 作为产物：
  描述：

  (3S)-N-[Boc-S-(p-methylbenzyl)-L-cysteinyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid 、 Cys(S-CH2C6H4-Me-p)-OBzl 在 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 14.0h， 以83%的产率得到N-[(3S)-N-(Boc-S-(p-methylbenzyl)-L-cysteinyl)-1,2,3,4-tetrahydroisoquinoline-3-carbonyl]-S-(p-methylbenzyl)-L-cysteine benzyl ester
  参考文献：
  名称：

  2,3-Diamino acid modifying 3S-tetrahydroisoquinoline-3-carboxylic acids: Leading to a class of novel agents with highly unfolded conformation, selective in vitro anti-platelet aggregation and potent in vivo anti-thrombotic activity

  摘要：

  In the preparation of anti-thrombotic agents the 2- and 3-positions of 3S-tetra-hydroisoquinoline-3-carboxylic acid (THIQA) were simultaneously modified with amino acids to form 20 novel N-(3S-N-amino-acyl-1,2,3,4-tetrahydroisoquinoline-3-carbonyl) amino acids (8a-t). On an in vitro platelet aggregation model 8a-t selectively inhibit ADP-induced platelet aggregation and their IC50 values are leas than 3.5 nM. On an extracorporeal circulation of arterioveinos cannula model of rats both orally and intraveously effective doses of 8a-t are less than 30 nmol/kg. Cerius(2) based stereoview of explores 8a-t having highly unfolded conformation. 3D QSAR analysis gives the importance of the unfolded conformation to high in vitro anti-platelet aggregation and in vivo anti-thrombotic potency rational understanding. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.01.009