3-(1-N-tert-butyloxycarbonylamino-2-hydroxyethyl)-benzoic acid methyl ester | 188586-95-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(1-N-tert-butyloxycarbonylamino-2-hydroxyethyl)-benzoic acid methyl ester
• 英文别名: Methyl 3-(1-{[(tert-butoxy)carbonyl]amino}-2-hydroxyethyl)benzoate；methyl 3-[2-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]benzoate
• CAS: 188586-95-0
• 化学式: C₁₅H₂₁NO₅
• 分子量: 295.335
• InChiKey: OESBPFWQMUIZNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(1-N-tert-butyloxycarbonylamino-2-hydroxyethyl)-benzoic acid methyl ester 在 盐酸 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 生成 (R,S)-2-amino-1-mercapto-2-(m-carboxyphenyl)ethane, hydrochloride
  参考文献：
  名称：

  Investigation of the Active Site of Aminopeptidase A Using a Series of New Thiol-Containing Inhibitors

  摘要：

  Aminopeptidase A (APA) and aminopeptidase N (APN) are two metallopeptidases which have been suggested to be involved in the enzymatic cascade of the renin-angiotensin system. APA liberates angotensin III from angiotensin II by releasing the N-terminal aspartate, and APN participates in the inactivation of angiotensin III. As the role of angiotensin III in the regulation of blood pressure in the central nervous system and at the periphery is controversial, it was of interest to develop selective and efficient inhibitors of APA. Starting from Glu-thiol,(1) which was the first efficient APA inhibitor described, but however is equipotent on APA (K-i = 0.14 mu M) and APN (K-i = 0.12 mu M), beta-amino thiols bearing various carboxyalkyl chains have been synthesized and their inhibitory potencies measured on both purified enzymes. Compounds containing a carboxylated aromatic ring inhibited APA and APN with K-i values in the micromolar range but were slightly more active on APA. Conversely, inhibitors containing a cyclohexyl ring were more efficient on APN. Various modifications of the structure of Glu-thiol decreased inhibitory activity on both enzymes but increased the selectivity for APA, and compound 9d ((S)-4-amino-6-mercaptohexanoic acid) was 23 times more potent on APA (K-i = 2.0 mu M) than on APN (K-i = 45 mu M).

  DOI：

  10.1021/jm00035a014
• 作为产物：
  描述：

  3-氰基苯甲醛 在 盐酸 、 sodium tetrahydroborate 、 氯化亚砜 、 lithium chloride 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 3-(1-N-tert-butyloxycarbonylamino-2-hydroxyethyl)-benzoic acid methyl ester
  参考文献：
  名称：

  Investigation of the Active Site of Aminopeptidase A Using a Series of New Thiol-Containing Inhibitors

  摘要：

  Aminopeptidase A (APA) and aminopeptidase N (APN) are two metallopeptidases which have been suggested to be involved in the enzymatic cascade of the renin-angiotensin system. APA liberates angotensin III from angiotensin II by releasing the N-terminal aspartate, and APN participates in the inactivation of angiotensin III. As the role of angiotensin III in the regulation of blood pressure in the central nervous system and at the periphery is controversial, it was of interest to develop selective and efficient inhibitors of APA. Starting from Glu-thiol,(1) which was the first efficient APA inhibitor described, but however is equipotent on APA (K-i = 0.14 mu M) and APN (K-i = 0.12 mu M), beta-amino thiols bearing various carboxyalkyl chains have been synthesized and their inhibitory potencies measured on both purified enzymes. Compounds containing a carboxylated aromatic ring inhibited APA and APN with K-i values in the micromolar range but were slightly more active on APA. Conversely, inhibitors containing a cyclohexyl ring were more efficient on APN. Various modifications of the structure of Glu-thiol decreased inhibitory activity on both enzymes but increased the selectivity for APA, and compound 9d ((S)-4-amino-6-mercaptohexanoic acid) was 23 times more potent on APA (K-i = 2.0 mu M) than on APN (K-i = 45 mu M).

  DOI：

  10.1021/jm00035a014

文献信息

• Gastrin and cholecystokinin receptor ligands(II)
  申请人：——

  公开号：US20030199565A1

  公开（公告）日：2003-10-23

  Substituted imidazoles (1) are useful as angiotensin II blockers. These compounds have activity in treating hypertension and congestive heart failure. Pharmaceutical compositions containing the novel imidazoles and pharmaceutical methods using them, alone and in conjunction with other drugs, especially diuretics and non-steroidal antiinflammatory drugs (NSAID's) are also described.

  取代咪唑（1）可作为血管紧张素II受体拮抗剂。这些化合物具有治疗高血压和充血性心力衰竭的活性。还描述了含有新型咪唑的药物组合物和使用它们的药物方法，单独或与其他药物一起使用，特别是利尿剂和非甾体抗炎药（NSAID）。
• Serine protease inhibitors
  申请人：——

  公开号：US20040259868A1

  公开（公告）日：2004-12-23

  Compounds of formula (I) 1 in which R 2 , X, Y, Cy, L and Lp(D) n have the meanings given in the specification, are inhibitors of the serine protease, Factor Xa and are useful in the treatment of cardiovascular disorders.

  式(I)的化合物，其中R2、X、Y、Cy、L和Lp(D)n的含义如规范中所述，是丝氨酸蛋白酶Xa的抑制剂，可用于治疗心血管疾病。
• Serine pretease inhibitors
  申请人：——

  公开号：US20030109706A1

  公开（公告）日：2003-06-12

  Compounds of formula (I) in which R 2 , X, Y, Cy, L and Lp(D) n have the meanings given in the specification, are inhibitors of the serine protease, Factor Xa and are useful in the treatment of cardiovascular disorders. 1

  式(I)的化合物中，R2、X、Y、Cy、L和Lp(D)nhave的含义如规范中所述，是丝氨酸蛋白酶抑制剂，可用于治疗心血管疾病。
• SERINE PROTEASE INHIBITORS
  申请人：ELI LILLY AND COMPANY

  公开号：EP1289950B1

  公开（公告）日：2004-09-08
• EP1510515A1
  申请人：——

  公开号：EP1510515A1

  公开（公告）日：2005-03-02