(2S)-3-phenylcarbonylthio-2-phenylmethylpropionic acid | 83024-49-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (2S)-3-phenylcarbonylthio-2-phenylmethylpropionic acid
• 英文别名: (S)-α-[(Benzoylthio)methyl]benzenepropanoic acid；(2S)-3-phenylcarbonyithio-2-phenylmethylpropionic acid；3-benzoylthio-2(S)-benzylpropionic acid；(S)-3-(benzoylthio)-2-benzylpropanoic acid；(2S)-2-(benzoylsulfanylmethyl)-3-phenylpropanoic acid
• CAS: 83024-49-1
• 化学式: C₁₇H₁₆O₃S
• 分子量: 300.378
• InChiKey: CZLYJRLSZIYXFG-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  79.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S)-3-phenylcarbonylthio-2-phenylmethylpropionic acid 在 sodium hydroxide 、 氯化亚砜 、 三乙胺 作用下， 以 甲醇 、 水 、 甲苯 、 乙腈 为溶剂， 反应 5.0h， 生成 (2S)-2-[[(2S)-2-benzyl-3-sulfanylpropanoyl]amino]-4-methylsulfanylbutanamide
  参考文献：
  名称：

  Mercaptoacyl aminoacid inhibitors of atriopeptidase. 1. Structure-activity relationship studies of methionine and S-alkylcysteine derivatives

  摘要：

  A broad series of N-(3-mercaptoacyl) amino acid derivatives was evaluated for their ability to inhibit atriopeptidase (neutral endopeptidase, EC 3.4.24.11) in vitro and in vivo. Structural parameters studied were (i) the substituent on the 2-position of the 3-mercaptopropionyl moiety, (ii) the amino acid component, (iii) the S-terminal derivative, and (iv) the C-terminal derivative. Optimum activity was observed for derivatives of methionine and S-alkylcysteines. N-[3-Mercapto-2(S)-[(2-methylphenyl)methyl]-1-oxopropyl]-L-methionine was identified as a highly effective inhibitor of atriopeptidase meriting evaluation as a potential cardiovascular therapeutic agent.

  DOI：

  10.1021/jm00041a026
• 作为产物：
  描述：

  2-[(benzoylthio)methyl]-3-phenylpropanoic acid 生成 (2S)-3-phenylcarbonylthio-2-phenylmethylpropionic acid
  参考文献：
  名称：

  逆向二肽的1 H NMR构型相关性：用于确定“脑啡肽酶”抑制剂的绝对构型。立体化学与酶识别之间的关系。

  摘要：

  噻吩[N- [2（RS）-（巯基甲基）-1-氧代-3-苯基丙基]甘氨酸]和噻吩基反[3-[[1（RS）-（巯基甲基）-2-苯基乙基]的立体定向合成。据报道，有两种高效的脑啡肽酶抑制剂，即一种参与脑啡肽代谢的中性内肽酶，即氨基] -3-氧代丙酸]。由于快速的异构化过程，不能通过经典方法分离包含2-取代的丙二酰基部分的反式-硫烷的衍生物。然而，通过HPLC实现了这些逆硫代硫烷衍生物的非对映异构体混合物的分离。通过使用NMR构型相关性确定每种异构体的绝对构型。各种抑制剂的抑制能力表明，在硫醇系列中，对脑啡肽酶的亲和力与2-（巯基甲基）-1-氧代-3-苯基丙基部分的立体化学无关。相反，在逆硫氰酸系列中，观察到两种对映体的抑制活性相差100倍。这表明在酶的活性位点上，这两种抑制剂的构象行为存在很大差异。

  DOI：

  10.1021/jm00155a027

文献信息

• Enantioselective tautomerization of a new metastable enol
  作者：Rüdiger Henze、Lucette Duhamel、Marie-Claire Lasne

  DOI：10.1016/s0957-4166(97)00408-4

  日期：1997.10

  A new metastable enol was prepared by the reaction of 2-benzyl acrolein with thiobenzoic acid in aprotic solvents. The enantioselective tautomerization of this enol was studied and enantiomeric excesses up to 71% were found. The absolute configuration of the resulting aldehyde was assigned.

  通过使2-苄基丙烯醛与硫代苯甲酸在非质子传递溶剂中反应，制备了一种新的亚稳态烯醇。研究了该烯醇的对映体选择性互变异构，发现对映体过量高达71％。确定了所得醛的绝对构型。
• Mercapto acyl aminoacid derivatives endowed with dual ACE-NEP inhibitory
  申请人：Zambon Group S.p.A.

  公开号：US05994539A1

  公开（公告）日：1999-11-30

  Compounds of formula ##STR1## wherein R, R.sub.1, R.sub.2, R.sub.3, R.sub.4, m and n have the meanings reported in the description, processes for their preparation and pharmaceutical compositions which contain them as active ingredients are described. The compounds of formula I are endowed with a mixed ACE-inhibitory and NEP-inhibitory activity and are useful in the treatment of cardiovascular diseases.

  描述了公式##STR1##的化合物，其中R、R.sub.1、R.sub.2、R.sub.3、R.sub.4、m和n的含义如说明书中所述，以及它们的制备过程和包含它们作为活性成分的药物组合物。公式I的化合物具有混合的ACE抑制剂和NEP抑制剂活性，并且在心血管疾病的治疗中有用。
• Thiol derivatives with metallopeptidase inhibitory activity
  申请人：Zambon Group S.p.A.

  公开号：US05760241A1

  公开（公告）日：1998-06-02

  Compounds of formula ##STR1## wherein R, R.sub.1, R.sub.2, R.sub.3, R.sub.4, m and n have the meanings reported in the description, processes for their preparation and pharmaceutical compositions which contain them as active ingredients are described. The compounds of formula I are endowed with a mixed ACE-inhibitory and NEP-inhibitory activity and are useful in the treatment of cardiovascular diseases.

  本文描述了化学式为##STR1##的化合物，其中R、R.sub.1、R.sub.2、R.sub.3、R.sub.4、m和n的含义如描述中所述，以及它们的制备方法和包含它们作为活性成分的药物组合物。公式I的化合物具有混合的ACE抑制剂和NEP抑制剂活性，并且在心血管疾病的治疗中有用。
• Mercapto-acylamino acid antihypertensives
  申请人：SCHERING CORPORATION

  公开号：EP0322633A1

  公开（公告）日：1989-07-05

  Novel mercapto-acylamino acids useful in the treatment of hypertension and combinations of mercapto-­acylamino acids and atrial natriuretic factors or angiotensin converting enzyme inhibitors useful for treating hypertension are disclosed.

  本研究公开了可用于治疗高血压的新型巯基乙酰氨基酸，以及可用于治疗高血压的巯基乙酰氨基酸与心房利钠因子或血管紧张素转换酶抑制剂的组合。
• NOVEL AMINO ACID DERIVATIVES HAVING N,N-DIALKYLAMINOPHENYL GROUP
  申请人：SANTEN PHARMACEUTICAL CO., LTD.

  公开号：EP0870762A1

  公开（公告）日：1998-10-14

  The present invention relates to novel amino acid derivatives having an N, N-dialkylaminophenyl group represented by the general formula [I]. wherein R1 represents a hydrogen atom, a lower alkyl group, a phenyl-lower alkyl group, a lower alkanoyl group or a benzoyl group, and each phenyl ring in the phenyl-lower alkyl group and the benzoyl group can be substituted by a halogen atom, a lower alkyl group or a lower alkoxy group; R2 represents a carboxyl group which can be converted into an ester, an amide or a hydroxamic acid; R3 represents a lower alkyl group; R4 represents a lower alkyl group; A1 represents a lower alkylene group which can be substituted by a phenyl group, and the phenyl group can be substituted by a halogen atom, a lower alkyl group or a lower alkoxy group; A2 represents a lower alkylene group; A3 represents a lower alkylene group; and "Z" represents a sulfur atom or an oxygen atom. The compounds have inhibitory effects on LTA4 hydrolase and are useful as medicines, in particular, therapeutic agents for inflammatory diseases such as rheumatic diseases, psoriasis, inflammatory intestinal diseases, gout and cystic fibrosis, in which LTB4 is concerned.

  本发明涉及具有通式 [I] 所代表的 N，N-二烷基氨基苯基的新型氨基酸衍生物。 其中 R1 代表氢原子、低级烷基、苯基低级烷基、低级烷酰基或苯甲酰基，苯基低级烷基和苯甲酰基中的每个苯基环可被卤素原子、低级烷基或低级烷氧基取代； R2 代表可转化为酯、酰胺或羟肟酸的羧基； R3 代表低级烷基 R4 代表一个低级烷基； A1 代表可被苯基取代的低级亚烷基，苯基可被卤素原子、低级烷基或低级烷氧基取代； A2 代表一个低级亚烷基 A3 代表一个低级亚烷基；以及 Z "代表硫原子或氧原子。 这些化合物对 LTA4 水解酶有抑制作用，可用作药物，特别是治疗与 LTB4 有关的炎症性疾病，如风湿病、牛皮癣、肠道炎症性疾病、痛风和囊性纤维化。