(S)-1-(2-mercaptoacetyl)pyrrolidine-2-carboxylic acid | 64805-47-6

• 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: (S)-1-(2-mercaptoacetyl)pyrrolidine-2-carboxylic acid
• 英文别名: 1-(2-Mercapto-1-oxoethyl)-L-proline；N-(2-mercaptoacetyl)-L-proline；1-(2-mercaptoacetyl)-L-proline；(2S)-1-(2-sulfanylacetyl)pyrrolidine-2-carboxylic acid
• CAS: 64805-47-6
• 化学式: C₇H₁₁NO₃S
• 分子量: 189.235
• InChiKey: ZFAIWAPKPKJWEP-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-1-(2-mercaptoacetyl)pyrrolidine-2-carboxylic acid 生成 (2S)-1-[2-[(2S)-2-benzamido-3-(5-methyl-1H-indol-3-yl)propanoyl]sulfanylacetyl]pyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  RYAN, JAMES W.;CHUNG, ALFRED

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl (S)-1-(2-(acetylthio)acetyl)pyrrolidine-2-carboxylate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以100%的产率得到(S)-1-(2-mercaptoacetyl)pyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  卡托普利类似物作为金属β-内酰胺酶抑制剂

  摘要：

  合成了许多卡托普利类似物，并作为金属β-内酰胺酶IMP-1的抑制剂进行了测试。结构活性研究表明，甲基对于活性并不重要，并且可以通过缩短巯基烷酰基侧链的长度来最好地提高这些抑制剂的效力。用羧酸取代硫醇基导致活性完全丧失，而延长羧酸根基团的长度导致效力降低。用脯氨酸环取代哌啶酸可以维持良好的活性。

  DOI：

  10.1016/j.bmcl.2016.02.007

文献信息

• (N-lower alkyl-3,5-dioxo-3-pyrrolidinyl)thioalkanoylpyrrolidine-and
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04179568A1

  公开（公告）日：1979-12-18

  Compounds having the formula ##STR1## wherein R.sub.1 and R.sub.4 each is hydrogen, lower alkyl or phenyl-lower alkyl; R.sub.2 is lower alkyl; R.sub.3 is hydrogen, hydroxy or lower alkyl; R.sub.5 is hydrogen or lower alkyl; m is 2 or 3; and n is 0, 1 or 2; are useful analytical tools.

  具有以下结构式的化合物##STR1##其中R.sub.1和R.sub.4分别是氢、较低的烷基或苯基-较低的烷基；R.sub.2是较低的烷基；R.sub.3是氢、羟基或较低的烷基；R.sub.5是氢或较低的烷基；m为2或3；n为0、1或2；这些化合物是有用的分析工具。
• Renal-selective prodrugs for control of renal sympathetic nerve activity in the treatment of hypertension
  申请人：G.D. Searle & Co.

  公开号：US20030220521A1

  公开（公告）日：2003-11-27

  Renal-selective prodrugs are described which are preferentially converted in the kidney to compounds capable of inhibiting synthesis of catecholamine-type neurotransmitters involved in renal sympathetic nerve activity. The prodrugs described herein are derived from inhibitor compounds capable of inhibiting one or more of the enzymes involved in catecholamine synthesis, such compounds being classifiable as tyrosine hydroxylase inhibitors, or as dopa-decarboxylase inhibitors, or as dopamine-&bgr;-hydroxylase inhibitors. These inhibitor compounds are linked to a chemical moiety, such as a glutamic acid derivative, by a cleavable bond which is recognized selectively by enzymes located predominantly in the kidney. The liberated inhibitor compound is then available in the kidney to inhibit one or more of the enzymes involved in catecholamine synthesis. Inhibition of renal catecholamine synthesis can suppress heightened renal nerve activity associated with sodium-retention related disorders such as hypertension. Conjugates of particular interest are glutamyl derivatives of dopamine-&bgr;-hydroxylase inhibitors, of which N-acetyl-&ggr;-glutamyl fusaric acid hydrazide (shown below) is preferred. 1

  本文描述了一种肾选择性的前药，其在肾脏中优先转化为能够抑制参与肾交感神经活动的儿茶酚型神经递质合成的化合物。本文所描述的前药来源于能够抑制儿茶酚合成中的一个或多个酶的抑制剂化合物，这些化合物可分类为酪氨酸羟化酶抑制剂，多巴脱羧酶抑制剂或多巴胺-&bgr;-羟化酶抑制剂。这些抑制剂化合物通过可被肾脏中大量存在的酶选择性识别的可裂解键与化学基团（如谷氨酸衍生物）连接。释放的抑制剂化合物然后可在肾脏中用于抑制儿茶酚合成中的一个或多个酶。抑制肾脏儿茶酚合成可抑制与钠潴留相关的疾病（如高血压）相关的增强肾脏神经活动。特别感兴趣的共轭物是多巴胺-&bgr;-羟化酶抑制剂的谷氨酰衍生物，其中N-乙酰-&ggr;-谷氨酰富萨酸肼（如下图所示）是首选。1
• Renal-selective prodrugs for control of renal smpathetic nerve activity in the treatment of hypertension
  申请人：G.D. Searle & Co.

  公开号：US20040101523A1

  公开（公告）日：2004-05-27

  Renal-selective prodrugs are described which are preferentially converted in the kidney to compounds capable of inhibiting synthesis of catecholamine-type neurotransmitters involved in renal sympathetic nerve activity. The prodrugs described herein are derived from inhibitor compounds capable of inhibiting one or more of the enzymes involved in catecholamine synthesis, such compounds being classifiable as tyrosine hydroxylase inhibitors, or as dopa-decarboxylase inhibitors, or as dopamine-&bgr;-hydroxylase inhibitors. These inhibitor compounds are linked to a chemical moiety, such as a glutamic acid derivative, by a cleavable bond which is recognized selectively by enzymes located predominantly in the kidney. The liberated inhibitor compound is then available in the kidney to inhibit one or more of the enzymes involved in catecholamine synthesis. Inhibition of renal catecholamine synthesis can suppress heightened renal nerve activity associated with sodium-retention related disorders such as hypertension. Conjugates of particular interest are glutamyl derivatives of dopamine-&bgr;-hydroxylase inhibitors, of which N-acetyl-&ggr;-glutamyl fusaric acid hydrazide (shown below) is preferred. 1

  本文描述了肾脏选择性前药，这些前药被优先转化为能够抑制与肾脏交感神经活动相关的儿茶酚类神经递质合成的化合物。所述前药源自能够抑制儿茶酚类合成中涉及的一个或多个酶的抑制剂化合物，这些化合物可分类为酪氨酸羟化酶抑制剂，或多巴脱羧酶抑制剂，或是多巴胺-β-羟化酶抑制剂。这些抑制剂化合物与化学基团（例如谷氨酸衍生物）通过可被肾脏内的酶特异性识别的可切断键连接。被释放的抑制剂化合物随后可在肾脏中抑制一个或多个涉及儿茶酚类合成的酶。抑制肾脏儿茶酚类合成可以抑制与钠潴留相关的疾病（如高血压）所伴随的过度肾脏神经活动。特别感兴趣的结合物是多巴胺-β-羟化酶抑制剂的谷氨酰衍生物，其中N-乙酰-γ-谷氨酰菌核酸酸肼（如下图所示）是首选。1
• Bicyclic oxo-thiolactones, pharmaceutical compositions containing them, processes for their preparation and compounds useful as intermediates for their preparation
  申请人：AMERICAN HOME PRODUCTS CORPORATION

  公开号：EP0017390A2

  公开（公告）日：1980-10-15

  Disclosed herein are bicyclic oxo-thiolactones of the formula: in which R, is hydrogen or lower alkyl; R2 and R3 are, independently, hydrogen, hydroxy, halogen, lower alkyl, lower alkoxy, or aryl; and R4, R5 and R6 are independently, hydrogen, lower alkyl, lower hydroxyalkyl, aryl or aryl-alkyl, except that R4 and R5 may not both be aryl These compounds act as inhibitors or angiotension converting enzyme and are useful as agents for the treatment of hypertension in mammals. The compounds are stable against oxidation of the sulphur. Also disclosed are methods of preparation of such compounds and novel intermediates having the formula where Ra is hydrogen or an amino protecting group, Rb is hydrogen or a carboxylic acid protecting group, n is 1 or 0 and their salts.

  此处公开的是式中的双环氧硫杂内酯： 其中 R 是氢或低级烷基；R2 和 R3 独立地是氢、羟基、卤素、低级烷基、低级烷氧基或芳基；R4、R5 和 R6 独立地是氢、低级烷基、低级羟基烷基、芳基或芳基烷基，但 R4 和 R5 不一定都是芳基。 这些化合物是血管紧张素转换酶的抑制剂，可作为治疗哺乳动物高血压的药物。这些化合物对硫的氧化很稳定。 还公开了制备此类化合物和新型中间体的方法，其式为 其中 Ra 为氢或氨基保护基团，Rb 为氢或羧酸保护基团，n 为 1 或 0 及其盐类。
• Angiotensin converting enzyme inhibitors
  申请人：UNIVERSITY OF MIAMI

  公开号：EP0036713A2

  公开（公告）日：1981-09-30

  Novel inhibitors of angiotensin converting enzyme having the general formula R-A-S-Z are disclosed as potent inhibitors of angiotensin converting enzyme and are useful anti-hypertensive agents.

  公开了通式为 R-A-S-Z 的新型血管紧张素转换酶抑制剂，它们是血管紧张素转换酶的强效抑制剂，也是有用的抗高血压药物。