HCl*Hyp-OBzl | 62147-27-7

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 脯氨酸类衍生物
• 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: HCl*Hyp-OBzl
• 英文别名: L-hydroxyproline benzyl ester hydrochloride；trans-4-hydroxy-L-proline benzyl ester hydrochloride；(trans)-4-hydroxy-L-proline, phenylmethyl ester, hydrochloride；benzyl (2S)-4-hydroxypyrrolidine-2-carboxylate;hydrochloride
• CAS: 62147-27-7
• 化学式: C₁₂H₁₅NO₃*ClH
• 分子量: 257.717
• InChiKey: LVYXMDJSWLEZMP-GQNCZFCYSA-N

物化性质

• 熔点：
  162-165 °C

计算性质

• 辛醇/水分配系数(LogP)：
  0.87
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  58.6
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• WGK Germany：
  3
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  HCl*Hyp-OBzl 在 palladium on activated charcoal N-甲基吗啉 、 氢气 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 25.0~40.0 ℃ 、392.24 kPa 条件下， 反应 107.25h， 生成 CF3COOH*H-Gln-S-EtA-Hyp-MeA-Phol
  参考文献：
  名称：

  Emerimicins III 和 IV 及其乙基丙氨酸 12 差向异构体。促进化学酶合成及其溶液结构的定性评价

  摘要：

  peptaibol 抗生素，emerimicin III 和 IV（Ac-Phe 1 -MeA 2 -MeA 3 -MeA 4 -Val 5 -Gly 6 -Leu 7 -MeA 8 -MeA 9 - Hyp 10 -Gln 11 -R-EtA 12 -Hyp 13 -Xxx 14 -Phol 15 ，其中 Xxx=Ala for emerimicin III 和 Xxx=MeA for emerimicin IV) 和它们的 EtA 12 差向异构体已经使用包括溶液相片段缩合和最终木瓜蛋白酶介导的偶联的组合方法合成1-6 和 7-15 片段

  DOI：

  10.1021/ja00037a010

文献信息

• Substituted 4-phenoxy or 4-phenylthio prolines
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04536501A1

  公开（公告）日：1985-08-20

  Compounds of the formula ##STR1## are disclosed. They possess angiotensin converting enzyme inhibition activity and diuretic activity and are therefore useful as antihypertensive agents.

  公式为##STR1##的化合物已被披露。它们具有抑制血管紧张素转换酶的活性和利尿作用，因此可用作降压药物。
• Macrocyclic lactams as inhibitors of atrial natriuretic factors (ANF)-degrading neutral endopeptidase (NEP)
  申请人：CIBA-GEIGY AG

  公开号：EP0544620A1

  公开（公告）日：1993-06-02

  The invention relates to macrocyclic lactam derivatives of formula I wherein R is hydrogen or acyl; m is an integer from 4 to 9 inclusive; n is 1 or 2; p is zero, 1 or 2; X is -CONH- or -NHCO-; Y is S, O or CH₂; R₁ is -COOH; or R₁ is in which R₂ is hydrogen, lower alkyl, aryl-lower alkyl, amino-lower alkyl, hydroxy-lower alkyl, acyloxy-lower alkyl, lower alkoxy-lower alkyl, mercapto-lower alkyl, lower alkyl-(thio, sulfinyl or sulfonyl)-lower alkyl, or carboxy-lower alkyl, R₃ is hydrogen or lower alkyl, and q is zero or an integer from 1 to 5 inclusive; or R₁ is in which R₄ is hydrogen, lower alkyl, lower alkoxy, hydroxy or acyloxy, and r is 1 or 2; or R₁ is in which s is 1 or 2; or R₁ is in which R₅ and R₆ independently represent hydrogen, lower alkyl, C₅- or C₆-cycloalkyl, (hydroxy-, acyloxy or lower alkoxy-) lower alkyl, carbocyclic or heterocyclic monocyclic aryl, or (hydroxy-, acyloxy- or alkoxy-) lower alkyloxy-lower alkyl; or R₅ and R₆ together with the nitrogen to which they are attached represent pyrrolidino, piperidino, morpholino, piperazino or N-alkylpiperazino; and macrocyclic sulfur and oxygen containing lactam ring isomers in which a CH₂ group of (CH₂)m in formula I is replaced by O or S, and Y represents CH₂; and pharmaceutically acceptable prodrug esters of any above said compound with a free carboxyl group; and pharmaceutically acceptable salts of any said compounds with a free acid or basic salt forming group; pharmaceutical compositions comprising said compounds; methods for the preparation of said compounds and for the preparation of intermediates; and methods of treating disorders in mammals which are responsive to the inhibition of neutral endopeptidases by administration of said compounds to mammals in need of such treatment.

  本发明涉及式 I 的大环内酰胺衍生物 其中 R 是氢或酰基；m 是 4 至 9（包括 9）的整数；n 是 1 或 2；p 是 0、1 或 2；X 是 -CONH- 或 -NHCO-；Y 是 S、O 或 CH₂；R₁ 是 -COOH；或 R₁ 是 其中 R₂ 是氢、低级烷基、芳基-低级烷基、氨基-低级烷基、羟基-低级烷基、酰氧基-低级烷基、低级烷氧基-低级烷基、巯基-低级烷基、低级烷基-（硫基、亚磺酰基或磺酰基）-低级烷基或羧基-低级烷基，R₃ 是氢或低级烷基，且 q 是零或 1 至 5（包括 5）的整数；或 R₁ 是 其中 R₄ 是氢、低级烷基、低级烷氧基、羟基或酰氧基，且 r 是 1 或 2；或 R₁ 是 其中 s 为 1 或 2；或 R₁ 是 其中R₅和R₆各自代表氢、低级烷基、C₅-或C₆-环烷基、(羟基-、酰氧基-或低级烷氧基-)低级烷基、碳环或杂环单环芳基或(羟基-、酰氧基-或烷氧基-)低级烷氧基-低级烷基；或 R₅ 和 R₆ 与它们所连接的氮一起代表吡咯烷基、哌啶基、吗啉基、哌嗪基或 N-烷基哌嗪基；以及大环硫氧内酰胺环异构体，其中式 I 中 (CH₂)m 的 CH₂ 基团被 O 或 S 取代，Y 代表 CH₂；以及上述任何化合物的药学上可接受的带有游离羧基的原药酯；以及任何上述化合物的药学上可接受的带有游离酸或碱性成盐基团的盐；包含上述化合物的药物组合物；制备上述化合物和制备中间体的方法；以及通过向需要治疗的哺乳动物施用上述化合物来治疗对中性内肽酶抑制有反应的哺乳动物疾病的方法。
• Stabilized minimal coiled-coil mimetics
  申请人：NEW YORK UNIVERSITY

  公开号：US10851133B2

  公开（公告）日：2020-12-01

  This invention relates to a macrostructure that includes an antiparallel coiled-coil structure shown below or a parallel coiled-coil structure shown below and described in the present application.

  本发明涉及一种宏观结构，它包括下图所示的反平行盘卷结构或下图所示的平行盘卷结构，并在本申请中进行了描述。
• Design and synthesis of an orally active macrocyclic neutral endopeptidase 24.11 inhibitor
  作者：Lawrence J. MacPherson、Erol K. Bayburt、Michael P. Capparelli、Regine S. Bohacek、Frank H. Clarke、Rajendra D. Ghai、Yumi Sakane、Carol J. Berry、Jane V. Peppard、Angelo J. Trapani

  DOI：10.1021/jm00076a009

  日期：1993.11

  A potent macrocyclic inhibitor of neutral endopeptidase (NEP) 24.11 was designed using a computer model of the active site of thermolysin. This 10-membered ring lactam represents a general mimic for any hydrophobic dipeptide in which the two amino acid side chains bind to an enzyme in a contiguous orientation. The parent 10-membered ring lactam was synthesized and exhibited excellent potency as an NEP 24.11 inhibitor (IC50 = 3 nM). In order to improve oral bioavailability, various functionality was attached to the macrocycle. These modifications lead to CGS 25155, an orally active NEP 24.11 inhibitor that slows down the degradation of the cardiac hormone atrial natriuretic factor, producing a lowering of blood pressure in the DOCA-salt rat model of hypertension.
• BOROPEPTIDE INHIBITORS OF THROMBIN WHICH CONTAIN A SUBSTITUTED PYRROLIDINE RING
  申请人：THE DU PONT MERCK PHARMACEUTICAL COMPANY

  公开号：EP0722449A1

  公开（公告）日：1996-07-24