2-Nitro-N-acetyl-phenylalanin | 91176-91-9

• 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: 2-Nitro-N-acetyl-phenylalanin
• 英文别名: N-Acetyl-(o-nitrophenyl)-DL-alanin；N-Acetyl-o-nitro-phenylalanin；Phenylalanine, N-acetyl-2-nitro-；2-acetamido-3-(2-nitrophenyl)propanoic acid
• CAS: 91176-91-9
• 化学式: C₁₁H₁₂N₂O₅
• 分子量: 252.227
• InChiKey: UKBCRYALIRJOEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-Nitro-N-acetyl-phenylalanin 在 palladium on activated charcoal 盐酸 、 氢氧化钾 、 锂硼氢 、 氯化亚砜 、 水 、 氢气 、 sodium cyanoborohydride 、 碳酸氢钠 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醇 、 水 、 乙酸乙酯 为溶剂， 60.0 ℃ 、101.33 kPa 条件下， 反应 146.0h， 生成 2-[2-(2-tert-Butoxycarbonylamino-3-hydroxy-propyl)-phenylamino]-3-methyl-butyric acid
  参考文献：
  名称：

  Synthesis, Conformation, and Biological Activity of Teleocidin Mimics, Benzolactams. A Clarification of the Conformational Flexibility Problem in Structure−Activity Studies of Teleocidins

  摘要：

  Tumor-promoter teleocidins and their active congeners (indolactams) are known to exist in an equilibrium between at least two conformational states in solution, the twist and sofa form, due to cis-trans isomerization of the amide bond and the steric effects of substituents on the nine-membered lactam ring. Benzolactam-Vs, in which the indole ring of indolactams is replaced with a benzene ring, were designed and synthesized in an attempt to reproduce the active conformation of teleocidins. Among these benzolactams, eight-membered lactams (benzolactam-V8) can only exist in the twist form, and 9- and 10-membered lactams (benzolactam-V9 and -V10) exist exclusively in the sofa form in solution. The stronger biological activity of benzolactam-V-8-310 than that of indolactam-V (IL-V) and the inactivity of benzolactam-V-9-310 for differentiation inducing activity of HL-60 clearly indicated that the twist form is close to the active conformation of teleocidins.

  DOI：

  10.1021/ja953578v
• 作为产物：
  描述：

  diethyl 2-acetamido-2-(2-nitrobenzyl)malonate 在 sodium hydroxide 、 水 作用下， 反应 4.17h， 生成 2-Nitro-N-acetyl-phenylalanin
  参考文献：
  名称：

  Synthesis, Conformation, and Biological Activity of Teleocidin Mimics, Benzolactams. A Clarification of the Conformational Flexibility Problem in Structure−Activity Studies of Teleocidins

  摘要：

  Tumor-promoter teleocidins and their active congeners (indolactams) are known to exist in an equilibrium between at least two conformational states in solution, the twist and sofa form, due to cis-trans isomerization of the amide bond and the steric effects of substituents on the nine-membered lactam ring. Benzolactam-Vs, in which the indole ring of indolactams is replaced with a benzene ring, were designed and synthesized in an attempt to reproduce the active conformation of teleocidins. Among these benzolactams, eight-membered lactams (benzolactam-V8) can only exist in the twist form, and 9- and 10-membered lactams (benzolactam-V9 and -V10) exist exclusively in the sofa form in solution. The stronger biological activity of benzolactam-V-8-310 than that of indolactam-V (IL-V) and the inactivity of benzolactam-V-9-310 for differentiation inducing activity of HL-60 clearly indicated that the twist form is close to the active conformation of teleocidins.

  DOI：

  10.1021/ja953578v

文献信息

• [EN] 3,4-DISUBSTITUTED-PHENYLSULPHONAMIDES AND THEIR THERAPEUTIC USE<br/>[FR] 3,4-PHENYLSULFAMIDES DISUBSTITUES ET LEUR UTILISATION THERAPEUTIQUE
  申请人：CHIROSCIENCE LIMITED

  公开号：WO1996036596A1

  公开（公告）日：1996-11-21

  (EN) 3,4-Disubstituted benzenesulphonamides of general formula (i) in which R4 represents a 5-or 6-membered saturated or unsaturated carbocyclic or heterocyclic ring to which ring is fused an aryl, hetereoaryl, carbocyclic or heterocyclic ring, in which either or both rings may optionally be substituted, and the other substituents are as defined in Claim 1, have therapeutic utility via phosphodiesterase IV inhibition.(FR) 3,4-benzènesulfamides disubstitués représentés par la formule générale (i) dans laquelle R4 représente un noyau hétérocyclique ou carbocyclique insaturé ou saturé à 5 ou 6 éléments, auquel est fusionné un noyau aryle, hétéroaryle, hétérocyclique ou carbocyclique, où un ou les deux noyaux peuvent éventuellement être substitués, les autres substituants étant tels qu'ils sont définis dans la revendication 1, et présentant une utilité thérapeutique étant donné qu'ils inhibent la phosphodiestérase IV.

  该段英文文本涉及二取代苯砜胺的结构及其在抑制抗磷酸化酶IV方面的治疗作用。该类化合物的通用分子式为(i)，其中R4代表一个5或6个碳的碳环（饱和或不饱和的碳环或杂环），与另一个环发生融合。这两个环中的一个或两个可能被进一步取代，具体替代基团的定义在前述说明中。这些化合物不仅具有药物作用，而且被证明可以通过抑制抗磷酸化酶IV发挥治疗效果。 该法语文本内容与英文描述的结构相同，提供了相同信息，适用于翻译参考。 chants une utilité thérapeutique due à leur capacity d'inhiber phophodiesterase IV.
• US6833382B2
  申请人：——

  公开号：US6833382B2

  公开（公告）日：2004-12-21
• Synthesis, Conformation, and Biological Activity of Teleocidin Mimics, Benzolactams. A Clarification of the Conformational Flexibility Problem in Structure−Activity Studies of Teleocidins
  作者：Yasuyuki Endo、Michihiro Ohno、Masaaki Hirano、Akiko Itai、Koichi Shudo

  DOI：10.1021/ja953578v

  日期：1996.1.1

  Tumor-promoter teleocidins and their active congeners (indolactams) are known to exist in an equilibrium between at least two conformational states in solution, the twist and sofa form, due to cis-trans isomerization of the amide bond and the steric effects of substituents on the nine-membered lactam ring. Benzolactam-Vs, in which the indole ring of indolactams is replaced with a benzene ring, were designed and synthesized in an attempt to reproduce the active conformation of teleocidins. Among these benzolactams, eight-membered lactams (benzolactam-V8) can only exist in the twist form, and 9- and 10-membered lactams (benzolactam-V9 and -V10) exist exclusively in the sofa form in solution. The stronger biological activity of benzolactam-V-8-310 than that of indolactam-V (IL-V) and the inactivity of benzolactam-V-9-310 for differentiation inducing activity of HL-60 clearly indicated that the twist form is close to the active conformation of teleocidins.