p-nitrophenyl ester of 4-penthyloxycinnamic acid | 88956-31-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: p-nitrophenyl ester of 4-penthyloxycinnamic acid
• 英文别名: p-nitrophenyl-p'-n-amyloxycinnamate；3-(4-Pentyloxy-phenyl)-acrylic acid 4-nitro-phenyl ester；(4-nitrophenyl) (E)-3-(4-pentoxyphenyl)prop-2-enoate
• CAS: 88956-31-4
• 化学式: C₂₀H₂₁NO₅
• 分子量: 355.39
• InChiKey: IXGUCWWJLYXTAD-VGOFMYFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  p-nitrophenyl ester of 4-penthyloxycinnamic acid 、 CPI 在 sodium hydride 作用下， 生成 methyl (1R,12S)-4-methyl-7-oxo-10-[(E)-3-(4-pentoxyphenyl)prop-2-enoyl]-5,10-diazatetracyclo[7.4.0.01,12.02,6]trideca-2(6),3,8-triene-3-carboxylate
  参考文献：
  名称：

  Synthesis and Antitumor Activity of Duocarmycin Derivatives:  A-Ring Pyrrole Compounds Bearing Cinnamoyl Groups

  摘要：

  A series of N-cinnamates of the A-ring pyrrole compound of duocarmycin were synthesized and evaluated for in vitro anticellular activity against HeLa S-3 cells and in vivo antitumor activity against murine sarcoma 180 in mice. The 4'-methoxy- and 4'-BocNH-cinnamates exhibited strong in vitro anticellular activity among the synthesized compounds. The ortho substitution of the 4'-methoxycinnamate did not affect the anticellular activity and contributed to an enhancement of water solubility. Most of the 8-O-(N,N-dialkylcarbamoyl) derivatives of the 4'-methoxycinnamates displayed remarkably superior in vivo antitumor activity to duocarmycin A or B2. Moreover, it is noteworthy that these 8-O-(N,N-dialkylcarbamoyl) derivatives exhibited significant antitumor activity at wider range of doses as compared with the A-ring pyrrole derivatives having the trimethoxyindole skeleton in segment B.

  DOI：

  10.1021/jm9606094
• 作为产物：
  描述：

  对硝基苯酚 、 trans-p-pentyloxycinnamoyl chloride 以 吡啶 为溶剂， 生成 p-nitrophenyl ester of 4-penthyloxycinnamic acid
  参考文献：
  名称：

  Lohar, M. J.; Dave, Jayrang S., Molecular Crystals and Liquid Crystals (1969-1991), 1984, vol. 103, p. 143 - 154

  摘要：

  DOI：

文献信息

• DC-89 derivatives
  申请人：KYOWA HAKKO KOGYO CO., LTD.

  公开号：EP0520435A2

  公开（公告）日：1992-12-30

  DC-89 derivatives represented by the formula: wherein X represents hydrogen or C02CH3; and is or wherein Z represents CI or Br; R represents hydrogen, CONR1R2 (in which R1 and R2 independently represent hydrogen, a straight-chain or branched alkyl group having 1 to 4 carbon atoms or phenyl) or (in which n represents an integer of 0 to 4; R3 represents CH2, oxygen, N-CH3, or N-CH2CONR1R2 in which R1 and R2 have the same significances as defined above); and W represents hydrogen or (in which W1 and W2 independently represent hydrogen or OR4 in which R4 represents a straight-chain or branched alkyl or alkenyl group having 1 to 4 carbon atoms), and pharmaceutically acceptable salts thereof have an excellent anti-tumor and antibacterial activity and are expected to be useful as anti-tumor compositions and antibacterial compositions.

  DC-89 衍生物用公式表示： 其中 X 代表氢或 C02 ；以及 是 或 其中 Z 代表 CI 或 Br；R 代表氢、CONR1R2（其中 R1 和 R2 独立地代表氢、具有 1 至 4 个碳原子的直链或支链烷基或苯基）或 (其中 n 代表 0 至 4 的整数；R3 代表 CH2、 氧、N-CH3 或 N- CONR1R2，其中 R1 和 R2 的意义与上述定义相同）；以及 W 代表氢或 (其中 W1 和 W2 独立地代表氢或 OR4，其中 R4 代表具有 1 至 4 个碳原子的直链或支链烷基或烯基），及其药学上可接受的盐具有优异的抗肿瘤和抗菌活性，有望用作抗肿瘤组合物和抗菌组合物。
• Lohar, J. M.; Dave, Jayrang. S., Molecular Crystals and Liquid Crystals (1969-1991), 1984, vol. 103, p. 181 - 192
  作者：Lohar, J. M.、Dave, Jayrang. S.

  DOI：——

  日期：——
• Studies on duocarmycin SA and its derivatives
  作者：Satoru Nagamura、Akira Asai、Eiji Kobayashi、Katsushige Gomi、Hiromitsu Saito

  DOI：10.1016/s0968-0896(96)00276-3

  日期：1997.3

  New duocarmycin SA derivatives have been synthesized and evaluated for in vitro anticellular activity against HeLa S-3 cells, and in vivo antitumor activity against murine sarcoma 180 in mice. The results suggested that the N,N-dialkylcarbamoyl derivatives bearing the p-methoxy cinnamoyl group, which was prepared from duocarmycin SA, showed good in vivo antitumor activities superior to native duocarmycin SA. (C) 1997 Elsevier Science Ltd.
• US5258383A
  申请人：——

  公开号：US5258383A

  公开（公告）日：1993-11-02