[(S)-1-((S)-1-Formyl-2-phenyl-ethylcarbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester | 52961-49-6

• 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-((S)-1-Formyl-2-phenyl-ethylcarbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester
• 英文别名: [(S)-1-((S)-1-Benzyl-2-oxo-ethylcarbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester；benzyl N-[(2S)-1-oxo-1-[[(2S)-1-oxo-3-phenylpropan-2-yl]amino]-3-phenylpropan-2-yl]carbamate
• CAS: 52961-49-6
• 化学式: C₂₆H₂₆N₂O₄
• 分子量: 430.503
• InChiKey: OIKITZBTDSAJQH-ZEQRLZLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  84.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(S)-1-((S)-1-Formyl-2-phenyl-ethylcarbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester 在 ammonium hydroxide 、 sodium azide 、 碘 、 zinc dibromide 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 benzyl N-[(2S)-1-oxo-3-phenyl-1-[[(1S)-2-phenyl-1-(2H-tetrazol-5-yl)ethyl]amino]propan-2-yl]carbamate
  参考文献：
  名称：

  Microwave-Assisted One-Pot Tandem Reactions for Direct Conversion of Primary Alcohols and Aldehydes to Triazines and Tetrazoles in Aqueous Media

  摘要：

  A series of primary alcohols and aldehydes were treated with iodine in ammonia water under microwave irradiation to give the intermediate nitriles, which without isolation underwent [2 + 3] cycloadditions with dicyandiamide and sodium azide to afford high yields of the corresponding triazines and tetrazoles, including the alpha-amino- and dipeptidyl tetrazoles in high optical purity.

  DOI：

  10.1021/jo0625352
• 作为产物：
  描述：

  N-苄氧羰基-L-苯丙氨酸 N-羟基琥珀酰亚胺酯 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 [(S)-1-((S)-1-Formyl-2-phenyl-ethylcarbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester
  参考文献：
  名称：

  Development of α-keto-based inhibitors of cruzain, a cysteine protease implicated in Chagas disease

  摘要：

  Trypanosoma cruzi, a protozoan parasite, is the causative agent of Chagas disease, a major cause of cardiovascular disease in many Latin American countries. There is an urgent need to develop an improved therapy due to the toxicity of existing drugs and emerging drug resistance. Cruzain, the primary cysteine protease of T cruzi, is essential for the survival of the parasite in host cells and therefore is an important target for the development of inhibitors as potential therapeutics. A novel series of alpha-ketoamide-, alpha-ketoacid-, alpha-ketoester-, and aldehyde-based inhibitors of cruzain has been developed. The inhibitors were identified by screening protease targeted small molecule libraries and systematically optimizing the P1, P2, P3, and P1 ' residues using specific structure-guided methods. A total of 20 compounds displayed picomolar potency in in vitro assays and three inhibitors representing different alpha-keto-based inhibitor scaffolds demonstrated anti-trypanosomal activity in cell culture. A 2.3 angstrom crystallographic structure of cruzain bound with one of the alpha-ketoester analogs is also reported. The structure and kinetic assay data illustrate the covalent binding, reversible inhibition mechanism of the inhibitor. Information on the compounds reported here will be useful in the development of new lead compounds as potential therapeutic agents for the treatment of Chagas disease and as biological probes to study the role that cruzain plays in the pathology. This study also demonstrates the validity of structure-guided approaches to focused library design and lead compound optimization. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.12.053

文献信息

• New renin-inhibitory peptides and their use
  申请人：SANKYO COMPANY LIMITED

  公开号：EP0152255A2

  公开（公告）日：1985-08-21

  Compounds of formula wherein R' represents alkyl having an α-amino or protected α-amino substituent and an aryl, heterocyclic or heterocyclic- dithio substituent; R2 represents a variety of aliphatic and cycloaliphatic hydrocarbon groups, which may be substituted; R3 represents isobutyl, sec-butyl, benzyl or (C3-CS cyclo- elkyl)methyl; and X represents a group of formula -CH(-A-R")-Y) (in which: A represents a single bond or an alkylene group: R4 represents an optionally protected carboxy group, an optionally N-substituted carbamoyl group, an optionally N-substituted carbazoyl group or an acyl group; and Y represents a hydroxy group, a mercapto group or a formyl group), or a group of formula -P(O)(R5)-OH (in which R5 represents an alkyl group having at least one optionally protected carboxy, N-substituted carbamoyl, optionally N-substituted carbazoyl, C2-C7 aliphatic carboxylic acyl or aromatic carboxylic acyl substituent)]; and their salts are renin inhibitors, which may be used in the treatment of angiotensin-induced hypertension.

  式中的化合物 式中 R'代表具有α-氨基或受保护α-氨基取代基的烷基，以及芳基、杂环或杂环-二硫代基； R2 代表各种可被取代的脂肪族和环脂族烃基； R3 代表异丁基、仲丁基、苄基或（C3-CS 环烷基）甲基；以及 X 代表式 -CH(-A-R")-Y)的基团 其中A 代表单键或亚烷基：R4 代表任选受保护的羧基、任选 N-取代的氨基甲酰基、任选 N-取代的咔唑酰基或酰基；Y 代表羟基、巯基或甲酰基），或 式中-P(O)(R5)-OH 的基团 (其中 R5 代表具有至少一个任选保护的羧基、N-取代的氨基甲酰基、任选 N-取代的咔唑酰基、C2-C7 脂肪族羧酰基或芳香族羧酰基取代基的烷基）]；它们的盐类是肾素抑制剂，可用于治疗血管紧张素诱导的高血压。
• Potent and specific immunoproteasome inhibitors
  申请人：Orlowski Z. Robert

  公开号：US20060241056A1

  公开（公告）日：2006-10-26

  Compounds and methods of selectively inhibiting an immunoproteasome are described. Also described are methods of treating a cancer, an inflammation, and/or an autoimmune disease and methods of suppressing endogenous antigenic peptide generation by administering to a subject in need of treatment thereof a therapeutic amount of an immunoproteasome specific inhibitor.

  描述了选择性抑制免疫蛋白酶体的化合物和方法。还描述了治疗癌症、炎症和/或自身免疫性疾病的方法，以及通过向需要治疗的受试者施用治疗量的免疫蛋白酶体特异性抑制剂来抑制内源性抗原肽生成的方法。
• CALPAIN INHIBITORS FOR THE TREATMENT OF NEURODEGENERATIVE DISEASES
  申请人：SANOFI WINTHROP, INC.

  公开号：EP0840614A1

  公开（公告）日：1998-05-13
• POTENT AND SPECIFIC IMMUNOPROTEASOME INHIBITORS
  申请人：The University of North Carolina at Chapel Hill

  公开号：EP1863513A2

  公开（公告）日：2007-12-12
• US4698329A
  申请人：——

  公开号：US4698329A

  公开（公告）日：1987-10-06