O-benzyl-trans-4-hydroxy-L-proline | 40350-84-3

• 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: O-benzyl-trans-4-hydroxy-L-proline
• 英文别名: (2S,4R)-4-(benzyloxy)pyrrolidine-2-carboxylic acid；trans-4-hydroxy-L-Pro-benzyl ester；L-Hyp(Bn)；N-Boc-L-Hyp(Bzl)-OH；(2S,4R)-4-phenylmethoxypyrrolidin-1-ium-2-carboxylate
• CAS: 40350-84-3
• 化学式: C₁₂H₁₅NO₃
• 分子量: 221.256
• InChiKey: RJFJRYVMVNICCP-MNOVXSKESA-N

物化性质

• 熔点：
  196-198 °C(Solv: water (7732-18-5))
• 沸点：
  388.1±42.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  16
• 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：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  O-benzyl-trans-4-hydroxy-L-proline 在 lithium aluminium tetrahydride 作用下， 生成 tert-butyl (2S,4R)-4-(benzyloxy)-2-formylpyrrolidine-1-carboxylate
  参考文献：
  名称：

  New entry to alicyclic amines via alkylative fragmentation of cyclic aminoaldehyde tosylhydrazones

  摘要：

  Tosylhydrazones of cyclic aminoaldehydes when exposed to aromatic and aliphatic Grignard reagents produce ring-opened acyclic unsaturated primary carbamates and carbamate alcohols in good yields. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01807-4
• 作为产物：
  描述：

  Boc-L-羟脯氨酸 在 盐酸 、 sodium hydride 、 sodium iodide 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 生成 O-benzyl-trans-4-hydroxy-L-proline
  参考文献：
  名称：

  Capped dipeptide phenethylamide inhibitors of the HCV NS3 protease

  摘要：

  The N-terminal aminoacid of phenethylamide tripeptide inhibitors of the hepatitis C virus NS3 protease can be replaced with an a-hydroxy acid to obtain more 'drug like' inhibitors with low micromolar activity. The preferred S-configuration of the capping residue can be explained by molecular modeling studies. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.032

文献信息

• [EN] HOMODETIC CYCLIC PEPTIDES TARGETING α4β7 1NTEGRIN<br/>[FR] PEPTIDES CYCLIQUES HOMODÉTIQUES CIBLANT L'INTÉGRINE α4β7
  申请人：ENCYCLE THERAPEUTICS INC

  公开号：WO2018205008A1

  公开（公告）日：2018-11-15

  There is described herein antagonists of α4β7 integrin, and more particularly cyclic peptide antagonists, such as compounds of formula (I).

  本文描述了α4β7整合素的拮抗剂，更具体地说是循环肽拮抗剂，例如式（I）化合物。
• AMIDINOANILINE DERIVATIVE
  申请人：AJINOMOTO CO., INC.

  公开号：US20130023563A1

  公开（公告）日：2013-01-24

  Provided are a novel amidine derivative having an activated blood coagulation factor X inhibitory activity, a production method thereof, a production intermediate therefor, and a pharmaceutical composition containing the amidine derivative. An amidinoaniline derivative represented by the following formula (1-1) or a pharmaceutically acceptable salt thereof: , and a pharmaceutical composition containing the amidinoaniline derivative or a pharmaceutically acceptable salt thereof.

  提供了一种具有活化血凝血因子X抑制活性的新型胍衍生物，其制备方法，制备中间体以及含有该胍衍生物的药物组合物。所述胍胺苯衍生物如下式（1-1）所代表或其药用可接受的盐：<在式（1-1）中，每个符号如描述中定义>，以及含有该胍胺苯衍生物或其药用可接受的盐的药物组合物。
• Bicyclic modulators of androgen receptor function
  申请人：——

  公开号：US20030055094A1

  公开（公告）日：2003-03-20

  The invention provides compounds of the formula I 1 wherein the substitutents are as described herein. Further provided are methods of using such compounds for the treatment of nuclear hormone receptor-associated conditions, such as age related diseases, for example sarcopenia, and also provided are pharmaceutical compositions containing such compounds.

  该发明提供了公式I1中的化合物，其中取代基如本说明所述。进一步提供了使用这些化合物治疗核激素受体相关疾病的方法，例如与年龄相关的疾病，例如肌少症，并且还提供了含有这些化合物的药物组合物。
• A benzotriazole-mediated route to protected marine-derived hetero-2,5-diketopiperazines containing proline
  作者：Olivier Nsengiyumva、Sadra Hamedzadeh、James McDaniel、Jocelyn Macho、Grant Simpson、Siva S. Panda、Khanh Ha、Iryna Lebedyeva、Hassan M. Faidallah、Manal Metgen AL-Mohammadi、C. Dennis Hall、Alan R. Katritzky

  DOI：10.1039/c5ob00023h

  日期：——

  Dipeptidoyl benzotriazolides containing proline were cyclized by triethylamine into 2,5-diketopiperazines.

  含脯氨酸的二肽苯并三唑酰胺被三乙胺环化成2,5-二酮哌嗪。
• Macrocyclic prolinyl acyl guanidines as inhibitors of β-secretase (BACE)
  作者：Kenneth M. Boy、Jason M. Guernon、Yong-Jin Wu、Yunhui Zhang、Joe Shi、Weixu Zhai、Shirong Zhu、Samuel W. Gerritz、Jeremy H. Toyn、Jere E. Meredith、Donna M. Barten、Catherine R. Burton、Charles F. Albright、Andrew C. Good、James E. Grace、Kimberley A. Lentz、Richard E. Olson、John E. Macor、Lorin A. Thompson

  DOI：10.1016/j.bmcl.2015.10.031

  日期：2015.11

  The synthesis, evaluation, and structure-activity relationships of a class of acyl guanidines which inhibit the BACE-1 enzyme are presented. The prolinyl acyl guanidine chemotype (7c), unlike compounds of the parent isothiazole chemotype (1), yielded compounds with good agreement between their enzymatic and cellular potency as well as a reduced susceptibility to P-gp efflux. Further improvements in

  介绍了抑制BACE-1酶的一类酰基胍的合成，评估和构效关系。与母体异噻唑化学类型（1）的化合物不同，脯氨酰基酰基胍化学类型（7c）产生的化合物在其酶促和细胞效能之间具有良好的一致性，并且对P-gp外排的敏感性降低。通过大环化策略实现了效力和P-gp比的进一步提高。给出了野生型小鼠体内的概况和大环类似物21c的P-gp效应。