benzyl 1-amino-1-cyclopentanoate hydrochloride

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl 1-amino-1-cyclopentanoate hydrochloride
• 英文别名: benzyl-1-amino-1-cyclopentanoate hydrochloride salt；Benzyl 1-aminocyclopentane-1-carboxylate;hydrochloride；benzyl 1-aminocyclopentane-1-carboxylate;hydrochloride
• 化学式: C₁₃H₁₇NO₂*ClH
• 分子量: 255.744
• InChiKey: DSHSXZLLJVYAJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  52.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl 1-amino-1-cyclopentanoate hydrochloride 在 吡啶 、 三乙胺 、 三氯氧磷 作用下， 以 乙酸乙酯 为溶剂， 反应 10.0h， 生成 (S)-benzyl 2-((2-((1-((benzyloxy)carbonyl)cyclopentyl)carbamoyl)-3-methylphenyl)carbamoyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  N-Prolinylanthranilamide Pseudopeptides as Bifunctional Organocatalysts for Asymmetric Aldol Reactions

  摘要：

  Proline anthranilamide-based pseudopeptides were shown to be effective organocatalysts for enantioselective direct aldol reactions of a selection of aldehydes with various ketones with excellent yield, enantioselectivity up to 99% and anti to syn diastereoselectivity up to 25:1.

  DOI：

  10.1021/ol202284n
• 作为产物：
  描述：

  (phenylmethyl) 1-[[(2-methylpropan-2-yl)oxy-oxomethyl]amino]-1-cyclopentanecarboxylate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 benzyl 1-amino-1-cyclopentanoate hydrochloride
  参考文献：
  名称：

  Toward the Back-Up of Boceprevir (SCH 503034): Discovery of New Extended P₄-Capped Ketoamide Inhibitors of Hepatitis C Virus NS3 Serine Protease with Improved Potency and Pharmacokinetic Profiles

  摘要：

  Hepatitis C is the most prevalent liver disease. Viral hepatitis C (HCV), a small (+)-RNA virus, infects chronically an estimated 300 million people worldwide. Results of Phase I clinical studies with our first generation HCV inhibitor Boceprevir, SCH 503034 (1), presented at the 56th Annual Meeting of the American Association for the Study of Liver Diseases (AASLD) were encouraging, and thus, additional human clinical studies are underway. In view of the positive data from our first generation compound, further work aimed at optimizing its overall profile was undertaken. Herein, we report that extension of our earlier inhibitor to the P-4 pocket and optimization of the P-1' capping led to the discovery of new ketoamide inhibitors of the HCV NS3 serine protease with improved in vitro potency. In addition to being potent inhibitors of HCV subgenomic RNA replication, some of the new P-4-capped inhibitors were also found to have improved PK profile.

  DOI：

  10.1021/jm801632a

文献信息

• [EN] CHEMICAL COMPOUNDS<br/>[FR] COMPOSES CHIMIQUES
  申请人：UNIV CARDIFF

  公开号：WO2005012327A2

  公开（公告）日：2005-02-10

  Phosphoramidate derivatives of nucleotides and their use in the treatment of cancer are described. The base moieties of, for example, each of deoxyuridine, cytarabine, gemcitabine and citidine may be substituted at the 5-position. The phosphoramidate moiety has attached to the P atom an aryl-O moiety and an α-amino acid moiety. The α-amino acid moiety may correspond to or be derived from either a naturally occurring or a non-naturally occurring amino acid.

  本文描述了核苷酸的磷酰胺衍生物及其在癌症治疗中的应用。例如，脱氧尿嘧啶，阿糖胞苷，吉西他滨和胞苷的碱基部分可以在5位位置上被替代。磷酰胺基团附着在P原子上，其中有一个芳基-O基团和一个α-氨基酸基团。α-氨基酸基团可以对应于或派生自天然存在或非天然存在的氨基酸。
• Chemical compounds
  申请人：McGuigan Christopher

  公开号：US20060142238A1

  公开（公告）日：2006-06-29

  Phosphoramidate derivatives of nucleotides and their use in the treatment of cancer are described. The base moieties of, for example, each of deoxyuridine, cytarabine, gemcitabine and citidine may be substituted at the 5-position. The phosphoramidate moiety has attached to the P atom an aryl-O moiety and an α-amino acid moiety. The a-amino acid moiety may correspond to or be derived from either a naturally occurring or a non-naturally occurring amino acid.

  本文介绍了核苷酸的磷酰胺衍生物及其在癌症治疗中的应用。例如，去氧尿嘧啶、阿糖胞苷、吉西他滨和胞苷的碱基部分可以在5-位被取代。磷酰胺基团附着在P原子上，有一个芳基-O基团和一个α-氨基酸基团。α-氨基酸基团可以对应于或派生自天然存在或非天然存在的氨基酸。
• [EN] NUCLEOTIDE PHOSPHORAMIDATES AS ANTICANCER AGENTS<br/>[FR] COMPOSES CHIMIQUES
  申请人：UNIV CARDIFF

  公开号：WO2005012327A3

  公开（公告）日：2005-04-21
• Anti-cancer ProTides: tuning the activity of BVDU phosphoramidates related to thymectacin
  作者：Christopher McGuigan、Jean-Christophe Thiery、Felice Daverio、Wen G. Jiang、Gaynor Davies、Malcolm Mason

  DOI：10.1016/j.bmc.2005.02.041

  日期：2005.5

  Based on our wide ranging knowledge of phosphoramidate ProTides as anti-viral agents we have tuned the lead anti-cancer agent thymectacin in the ester and amino acid regions and revealed a substantial enhancement in in vitro potency versus colon and prostate cancer cell lines. Twelve analogues have been reported, with yields of 29-78%. The compounds are fully characterised and data clearly reveal the presence of two phosphate diastereoisomers, as expected, in roughly equi-molar proportions. The compounds were evaluated in tissue culture versus three different tumour cell lines, using thymectacin as the control. It is notable that minor structural modification of the parent phenyl methoxyalaninyl structure of thymectacin leads to significant enhancements in potency. In particular, replacement of the methyl ester moiety in the lead by a benzyl ester gave a 175-fold boost in potency versus colon cancer HT115. This derivative emerges as a low micromolar inhibitor of HT115 cells and a new lead for further optimisation. (c) 2005 Elsevier Ltd. All rights reserved.
• NUCLEOTIDE PHOSPHORAMIDATES AS ANTICANCER AGENTS
  申请人：Nucana Biomed Limited

  公开号：EP1646639B1

  公开（公告）日：2016-08-17