N^α-(2-naphthylsulfonyl)-3-cyano-DL-phenylalanyl chloride | 80852-52-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N^α-(2-naphthylsulfonyl)-3-cyano-DL-phenylalanyl chloride
• CAS: 80852-52-4
• 化学式: C₂₀H₁₅ClN₂O₃S
• 分子量: 398.87
• InChiKey: CJLFYZHHXVUETR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  87.03
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N^α-(2-naphthylsulfonyl)-3-cyano-DL-phenylalanyl chloride 在 盐酸 、 氨 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 为溶剂， 反应 101.0h， 生成 3-[3-(4-Cyclohexanecarbonyl-piperazin-1-yl)-2-(naphthalene-2-sulfonylamino)-3-oxo-propyl]-benzamidine
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of Potent Thrombin Inhibitors:  Piperazides of 3-Amidinophenylalanine

  摘要：

  Thrombin is the key enzyme in the blood coagulation system, and inhibitors of its proteolytic activity are of therapeutic interest since they are potential anticoagulants. The most potent inhibitor of the benzamidine type is N-alpha-[(2-naphthylsulfonyl)glycyl]-4-amidinophenylalanylpiperidide (NAPAP). However, NAPAP and other benzamidine derivatives do not show favorable pharmacological properties; above all, they have very low systemic bioavailability after oral administration. The goal of designing new compounds was to obtain potent inhibitors with improved pharmacokinetic properties. Piperazide derivatives of 3-amidinophenylalanine as the key building block were synthesized. The piperazine moiety opened the possibility to introduce quite different substituents on the second nitrogen using common synthetic procedures. Some of the newly synthesized compounds are potent inhibitors of thrombin and offer an approach to study structure-function relationships for inhibition of thrombin and related enzymes and for the improvement of their pharmacokinetic properties.

  DOI：

  10.1021/jm960668h
• 作为产物：
  描述：

  Nα-(2-Naphthylsulfonyl)-3-carbamoylphenylalanin 在 氯化亚砜 作用下， 反应 1.0h， 生成 N^α-(2-naphthylsulfonyl)-3-cyano-DL-phenylalanyl chloride
  参考文献：
  名称：

  Wagner; Horn; Richter, Pharmazie, 1981, vol. 36, # 9, p. 597 - 603

  摘要：

  DOI：