(S)-1-[(4-chlorophenyl)acetyl]pyrrolidine-2-carboxylic acid

• 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)-1-[(4-chlorophenyl)acetyl]pyrrolidine-2-carboxylic acid
• 英文别名: (2S)-1-[2-(4-chlorophenyl)acetyl]pyrrolidine-2-carboxylic acid
• 化学式: C₁₃H₁₄ClNO₃
• mdl: MFCD16377076
• 分子量: 267.712
• InChiKey: LBMMRXHGBYDAJB-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.384
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对氯苯乙酰氯 、 L-脯氨酸 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.55h， 以78%的产率得到(S)-1-[(4-chlorophenyl)acetyl]pyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  Synthesis, Characterization and Antimicrobial Activity of N-2-(4-Chlorophenyl)acetyl Derivatives of (S)-Amino Acids

  摘要：

  本文报告了N-2-(4-氯苯基)乙酰衍生物的合成、表征和抗菌活性，这些衍生物是各种(S)-氨基酸的衍生物，如(S)-丙氨酸、(S)-苯丙氨酸、(S)-亮氨酸、(S)-蛋氨酸、(S)-脯氨酸和(S)-色氨酸。这些化合物已成功合成，并通过1H核磁共振、13C核磁共振和傅里叶变换红外光谱确认了它们的结构。这六种(S)-氨基酸衍生物的抗菌活性已通过琼脂孔扩散法评估，针对革兰氏阳性菌(S. aureus)、革兰氏阴性菌(K. aerogenes、E. coli和P. desmolyticumas)以及真菌(A. flavus和C. albicans)。所有这些化合物均表现出轻度至中度的抗菌活性。

  DOI：

  10.14233/ajchem.2020.22416

文献信息

• Nitrile derivatives that inhibit cathepsin K
  申请人：——

  公开号：US20010008901A1

  公开（公告）日：2001-07-19

  Compounds of the formula: 1 wherein R 1 to R 7 and Y are as defined in the specification, and pharmaceutically acceptable salts and/or pharmaceutically acceptable esters thereof, are useful for treating diseases associated with cystein proteases, such as osteoporosis, osteoarthritis, rheumatoid arthritis, tumor metastasis, glomerulonephritis, atherosclerosis, myocardial infarction, angina pectoris, instable angina pectoris, stroke, plaque rupture, transient ischemic attacks, amaurosis fugax, peripheral arterial occlusive disease, restenosis after angioplasty and stent placement, abdominal aortic aneurysm formation, inflammation, autoimmune disease, malaria, ocular fundus tissue cytopathy and respiratory disease.

  该公式化合物：其中R1到R7和Y如规范中定义，并且其药用盐和/或药用酯是用于治疗与半胱氨酸蛋白酶相关的疾病，如骨质疏松症、骨关节炎、类风湿性关节炎、肿瘤转移、肾小球肾炎、动脉粥样硬化、心肌梗死、心绞痛、不稳定性心绞痛、中风、斑块破裂、短暂性缺血性发作、瞬间性视网膜动脉阻塞、外周动脉闭塞性疾病、血管成形术和支架植入术后再狭窄、腹主动脉瘤形成、炎症、自身免疫疾病、疟疾、眼底组织细胞病变和呼吸道疾病的有用化合物。
• NITRILE DERIVATIVES AS CATHEPSIN K INHIBITORS
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1244621A1

  公开（公告）日：2002-10-02
• US6531612B2
  申请人：——

  公开号：US6531612B2

  公开（公告）日：2003-03-11
• [EN] NITRILE DERIVATIVES AS CATHEPSIN K INHIBITORS<br/>[FR] DERIVES DU NITRILE EN TANT QU'INHIBITEURS DE LA CATHEPSINE K
  申请人：HOFFMANN LA ROCHE

  公开号：WO2001047886A1

  公开（公告）日：2001-07-05

  The present invention relates to compounds of formula (I), wherein R1 to R7 and Y are as defined in the description and claims and pharmaceutically acceptable salts and/or pharmaceutically acceptable esters thereof. The compounds are useful for the treatment of diseases which are associated with cystein proteases such as osteoporosis, osteoarthritis, rheumatoid arthritis, tumor metastasis, glomerulonephritis, atherosclerosis, myocardial infarction, angina pectoris, instable angina pectoris, stroke, plaque rupture, transient ischemic attacks, amaurosis fugax, peripheral arterial occlusive disease, restenosis after angioplasty and stent placement, abdominal aortic aneurysm formation, inflammation, autoimmune disease, malaria, ocular fundus tissue cytopathy and respiratory disease.
• Synthesis, Characterization and Antimicrobial Activity of N-2-(4-Chlorophenyl)acetyl Derivatives of (S)-Amino Acids
  作者：G. Venkateshappa、P. Raghavendra Kumar、Krishna2

  DOI：10.14233/ajchem.2020.22416

  日期：2020.1.15

  This paper reports the synthesis, characterization and antibacterial activity of N-2-(4-chlorophenyl)acetyl derivatives of various (S)-amino acids such as (S)-alanine, (S)-phenylalanine, (S)-leucine, (S)-methionine, (S)-proline and (S)-tryptophane. These compounds have been successfully synthesized and their structures were confirmed by 1H NMR and 13C NMR and FT-IR spectroscopy. The antimicrobial activity of these six (S)-amino acids derivatives have been evaluated by the agar well diffusion method against pathogens both Gram-positive (S. aureus) and Gram-negative (K. aerogenes, E. coli and P. desmolyticumas) bacteria and fungi (A. flavus and C. albicans). All these compounds have shown mild to moderate antimicrobial activity.

  本文报告了N-2-(4-氯苯基)乙酰衍生物的合成、表征和抗菌活性，这些衍生物是各种(S)-氨基酸的衍生物，如(S)-丙氨酸、(S)-苯丙氨酸、(S)-亮氨酸、(S)-蛋氨酸、(S)-脯氨酸和(S)-色氨酸。这些化合物已成功合成，并通过1H核磁共振、13C核磁共振和傅里叶变换红外光谱确认了它们的结构。这六种(S)-氨基酸衍生物的抗菌活性已通过琼脂孔扩散法评估，针对革兰氏阳性菌(S. aureus)、革兰氏阴性菌(K. aerogenes、E. coli和P. desmolyticumas)以及真菌(A. flavus和C. albicans)。所有这些化合物均表现出轻度至中度的抗菌活性。