1-benzylpyrrolidine-3,4-dicarboxylic acid | 164916-63-6

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1-benzylpyrrolidine-3,4-dicarboxylic acid
• 英文别名: (3R,4S)-1-benzylpyrrolidine-3,4-dicarboxylic acid；(3S,4R)-1-benzylpyrrolidine-3,4-dicarboxylic acid
• CAS: 164916-63-6
• 化学式: C₁₃H₁₅NO₄
• 分子量: 249.266
• InChiKey: DFAFONDGWHOURT-PHIMTYICSA-N

物化性质

• 熔点：
  211-212 °C
• 沸点：
  460.0±45.0 °C(Predicted)
• 密度：
  1.365±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  77.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-benzylpyrrolidine-3,4-dicarboxylic acid 在 乙酸酐 、 溶剂黄146 作用下， 以91%的产率得到cis-5-benzyltetrahydro-1H-furo[3,4-c]pyrrole-1,3(3aH)-dione
  参考文献：
  名称：

  Synthesis and biological activity of Δ-5,6-norcantharimides: importance of the 5,6-bridge

  摘要：

  Cantharidin (1) and norcantharidin (2) are potent protein phosphatase 1 and 2A inhibitors that also display high levels of anticancer activity against a broad range of tumor cells lines. Surprisingly, Delta-5,6-ethyl norcantharidin (3, cis-tetrahydrofurano[3,4-c]furan-1,3-dione) displays neither phosphatase inhibition nor anticancer activity. This suggests that the 5,6-ethyl bridge is pivotal to both anti-cancer and protein phosphatase activity. Additionally bioisosteric replacement of the ethereal oxygen has no effect on biological activity nor does modification of the anhydride moiety. Unlike the parent norcantharidin. anhydride ring opening has no effect on either protein phosphatase inhibition or anti-cancer activity. Additionally, this work highlights the discovery of the octyl substituted, cis-5-benzyl-2-hexyltetrahydro-2H,3aH-pyrrolo[3,4-c]pyrrole-1,3-dione, 9p, and the octyl substituted, cis-octyltetrahydro-5H-furo[3,4-c]pyrrole-4,6-dione, 8p, as two new cytotoxic agents which are equipotent (9p) with, and more potent (8p) than norcantharidin. Crown Copyright (C) 2010 Published by Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.01.004
• 作为产物：
  描述：

  顺式-二甲基 1-苄基吡咯烷-3,4-二羧酸 在 盐酸 、 水 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 22.0h， 以69%的产率得到1-benzylpyrrolidine-3,4-dicarboxylic acid
  参考文献：
  名称：

  Synthesis and biological activity of Δ-5,6-norcantharimides: importance of the 5,6-bridge

  摘要：

  Cantharidin (1) and norcantharidin (2) are potent protein phosphatase 1 and 2A inhibitors that also display high levels of anticancer activity against a broad range of tumor cells lines. Surprisingly, Delta-5,6-ethyl norcantharidin (3, cis-tetrahydrofurano[3,4-c]furan-1,3-dione) displays neither phosphatase inhibition nor anticancer activity. This suggests that the 5,6-ethyl bridge is pivotal to both anti-cancer and protein phosphatase activity. Additionally bioisosteric replacement of the ethereal oxygen has no effect on biological activity nor does modification of the anhydride moiety. Unlike the parent norcantharidin. anhydride ring opening has no effect on either protein phosphatase inhibition or anti-cancer activity. Additionally, this work highlights the discovery of the octyl substituted, cis-5-benzyl-2-hexyltetrahydro-2H,3aH-pyrrolo[3,4-c]pyrrole-1,3-dione, 9p, and the octyl substituted, cis-octyltetrahydro-5H-furo[3,4-c]pyrrole-4,6-dione, 8p, as two new cytotoxic agents which are equipotent (9p) with, and more potent (8p) than norcantharidin. Crown Copyright (C) 2010 Published by Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.01.004

文献信息

• PEPTIDE DEFORMYLASE INHIBITORS
  申请人：Qin Donghui

  公开号：US20090306066A1

  公开（公告）日：2009-12-10

  The present invention is directed to certain 2-(alkyl)-3-[2-(5-fluoro-4-pyrimidinyl)hydrazino]-3-oxopropyl}hydroxyformamide derivatives, compositions containing them, the use of such compounds in the inhibition of bacterial peptide deformylase (PDF) activity, and in the treatment of bacterial infections. Specifically, the invention is directed to compounds of formula (I): wherein R1, R2 and R3 are defined herein and to pharmaceutically acceptable salts thereof. The compounds of this invention are bacterial peptide deformylase inhibitors and can be useful in the treatment of bacterial infections.

  本发明涉及某些2-(烷基)-3-[2-(5-氟-4-嘧啶基)肼基]-3-氧代丙基}羟基甲酰胺衍生物，包含它们的组合物，这些化合物在抑制细菌肽变形酶（PDF）活性和治疗细菌感染方面的使用。具体而言，本发明涉及式（I）的化合物：其中R1，R2和R3在此定义，并且其药学上可接受的盐。本发明的化合物是细菌肽变形酶抑制剂，可用于治疗细菌感染。
• BICYCLIC OXAZINE AND THIAZINE OXAZOLIDINONE ANTIBACTERIALS
  申请人：PHARMACIA & UPJOHN COMPANY

  公开号：EP0792273A1

  公开（公告）日：1997-09-03
• US5952324A
  申请人：——

  公开号：US5952324A

  公开（公告）日：1999-09-14
• US7893056B2
  申请人：——

  公开号：US7893056B2

  公开（公告）日：2011-02-22
• [EN] FUNGICIDES<br/>[FR] FONGICIDES
  申请人：ZENECA LIMITED

  公开号：WO1995007022A1

  公开（公告）日：1995-03-16

  (EN) A method of combating fungi which comprises applying to a plant, to a seed of a plant or to the locus of a seed or plant a compound of formula (I), wherein X is O, S, SO, SO2, NR8 or CLM; A, B, D, E, L and M are, independently, hydrogen, halogen, alkyl, mono- or di-haloalkyl, benzyl (optionally substituted by halogen or haloalkyl) or hydroxy; A and B or D and E or L and M may together form a =S, =O or =CR6R7 group; B and L or D and L may together form a bond; V is O or NR4; R1 and R2 are, independently, hydrogen or an amine protecting group; R3, R4 and R8 are, independently, hydrogen, alkyl or benzyl; R6 and R7 are, independently, hydrogen, halogen, alkyl, phenyl, benzyl, alkoxy or acyloxy; or a salt thereof; provided that when X is CLM, R1, R2, R3, A, M, D and E are all hydrogen, L and B are either both hydrogen or together form a bond, and V is O then the compound of formula (I) is in the form of a salt, but not a hydrochloride salt.(FR) L'invention concerne un procédé de lutte contre les champignons, qui comprend l'application sur une plante, sur une graine d'une plante ou sur le site de la graine ou de la plante, d'un composé de formule (I), dans laquelle X représente O, S, SO, SO2, NR8 ou CLM; A, B, D, E, L et M représentent indépendamment hydrogène, halogène, alkyle, mono- ou di-haloalkyle, benzyle (facultativement substitué par halogène ou haloalkyle) ou hydroxy; A et B ou D et E ou L et M peuvent former ensemble un groupe =S, =O ou =CR6R7; B et L ou D et L peuvent former ensemble une liaison; V représente O ou NR4; R1 et R2 représentent indépendamment hydrogène ou un groupe protecteur d'amines; R3, R4 et R8 représentent indépendamment hydrogène, alkyle ou benzyle; R6 et R7 représentent indépendamment hydrogène, halogène, alkyle, phényle, benzyle, alcoxy or acyloxy; ou un de leurs sels; à condition que lorsque X représente CLM, R1, R2, R3, A, M, D et E représentent tous hydrogène, L et B soit représentent tous deux hydrogène soit forment ensemble une liaison, et V représente O, alors, le composé de la formule (I) est sous la forme d'un sel qui n'est pas un sel de chlorhydrate.