(E)-N^α-Ac-3,4-didehydro-D,L-ornithine | 123164-74-9

• 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: (E)-N^α-Ac-3,4-didehydro-D,L-ornithine
• 英文别名: (E)-2-acetoamido-5-amino-3-pentenoic acid；(E)-5-amino-2-acetamido-3-pentenoic acid；(E)-2-acetamido-5-aminopent-3-enoic acid
• CAS: 123164-74-9
• 化学式: C₇H₁₂N₂O₃
• 分子量: 172.184
• InChiKey: HFYXKIHZUAJICX-NSCUHMNNSA-N

物化性质

• 熔点：
  200-205 °C (decomp)
• 沸点：
  487.3±45.0 °C(Predicted)
• 密度：
  1.209±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  92.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-N^α-Ac-3,4-didehydro-D,L-ornithine 生成 (E,2S)-2,5-diaminopent-3-enoic acid
  参考文献：
  名称：

  TOLMAN, V.;SEDMERA, P., TETRAHEDRON LETT., 29,(1988) N 47, C. 6183-6184

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl (E)-2-acetamido-5-phthalimido-2-ethoxycarbonyl-3-pentenoate 在 sodium hydroxide 作用下， 反应 12.0h， 以44%的产率得到(E)-N^α-Ac-3,4-didehydro-D,L-ornithine
  参考文献：
  名称：

  Havlicek, Libor; Hanus, Jan; Sedmera, Petr, Collection of Czechoslovak Chemical Communications, 1990, vol. 55, # 8, p. 2074 - 2085

  摘要：

  DOI：

文献信息

• Inhibitors of nitric oxide biosynthesis
  申请人：MERRELL PHARMACEUTICALS INC.

  公开号：EP0446699A1

  公开（公告）日：1991-09-18

  The present invention is directed to a new class of compound which are useful as inhibitors of the biosynthesis of nitric oxide.

  本发明涉及一类可用作一氧化氮生物合成抑制剂的新型化合物。
• Havlicek, Libor; Hanus, Jan; Nemecek, Jan, Collection of Czechoslovak Chemical Communications, 1989, vol. 54, # 12, p. 3381 - 3386
  作者：Havlicek, Libor、Hanus, Jan、Nemecek, Jan

  DOI：——

  日期：——
• Unsaturated amino acids: Synthesis of trans-3,4-didehydro analogues of L-ornithine and L-arginine
  作者：V. Tolman、P. Sedmera

  DOI：10.1016/s0040-4039(00)82302-3

  日期：——
• Conformationally-restricted arginine analogues as alternative substrates and inhibitors of nitric oxide synthases
  作者：Younghee Lee、Michael A. Marletta、Pavel Martasek、Linda J. Roman、Bettie Sue Siler Masters、Richard B. Silverman

  DOI：10.1016/s0968-0896(99)00029-2

  日期：1999.6

  Conformationally restricted arginine analogues (1-5) were synthesized and found to be alternative substrates or inhibitors of the three isozymes of nitric oxide synthase (NOS). A comparison of k(cat)/K-m values shows that (E)-3,4-didehydro-D,L-arginine(1) is a much better substrate than the corresponding (Z)-isomer (2) and 3-guanidino-D,L-phenylglycine (3), although none is as good a substrate as is arginine; 5-keto-D,L-arginine (4) is not a substrate, but is an inhibitor of the three isozymes. Therefore, it appears that arginine binds to all of the NOS isozymes in an extended (E-like) conformation. None of the compounds exhibits time-dependent inhibition of NOS, but they are competitive reversible inhibitors. Based on the earlier report that NW-propyl-L-arginine is a highly selective nNOS inhibitor (Zhang, H. Q.; Fast, W.; Marletta, M.; Martasek, P.; Silverman, R. B. J. Med. Chem. 1997, 40, 3869), (E)-N-omega-propyl-3,4-didehydro-D,L-arginine (5) was synthesized, but it was shown to be weakly potent and only a mildly selective inhibitor of NOS. Imposing conformational rigidity on an arginine backbone does not appear to be a favorable approach for selective NOS inhibition. (C) 1999 Elsevier Science Ltd. All rights reserved.
• HALVICEK, LIBOR;HANUS, JAN;NEMECEK, JAN, COLLECT. CZECHOSL. CHEM. COMMUN., 54,(1989) N2, C. 3381-3386
  作者：HALVICEK, LIBOR、HANUS, JAN、NEMECEK, JAN

  DOI：——

  日期：——