2-amino-4-(2-nitrophenyl)butyric acid | 105260-07-9

• 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-amino-4-(2-nitrophenyl)butyric acid
• 英文别名: 2-amino-4-(2-nitrophenyl)butanoic acid
• CAS: 105260-07-9
• 化学式: C₁₀H₁₂N₂O₄
• 分子量: 224.216
• InChiKey: ANELVGMNCPNANJ-UHFFFAOYSA-N

物化性质

• 沸点：
  398.7±37.0 °C(Predicted)
• 密度：
  1.352±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-amino-4-(2-nitrophenyl)butyric acid 在 palladium on activated charcoal 氢氧化钾 、 锂硼氢 、 氯化亚砜 、 氢气 、 sodium cyanoborohydride 、 碳酸氢钠 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 172.33h， 生成
  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：

  2-硝基苯乙基溴 在 盐酸 、 sodium hydride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 2-amino-4-(2-nitrophenyl)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

文献信息

• Piperidine derivatives
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04816466A1

  公开（公告）日：1989-03-28

  Novel Compounds of the formula: ##STR1## [wherein A is an .alpha.-amino acid residue; B is a group represented by the formula: ##STR2## (wherein R.sup.4 is hydrogen, lower alkyl, aralkyl or amino-lower alkyl), whereby the linkage between the symbols A and B designates a peptide bond and the group R.sup.4 is B may be linked with A; R.sup.1 is hydrogen, lower alkyl or aralkyl; R.sup.2 is hydrogen, lower alkyl, aralkyl or acyl; X is alkylene] and salts thereof posses, for example, inhibitory activity on angiotension converting enzyme, and are useful as an agent for diagnosis, prevention or treatment of hypertension as well as circulatory diseases such as cardiopathy and cerebral apoplexy.

  具有以下结构的新化合物：##STR1## [其中A是一个α-氨基酸残基；B是一个由以下结构表示的基团：##STR2##（其中R.sup.4是氢、低碳基、芳基碳基或氨基低碳基），其中符号A和B之间的连接表示肽键，基团R.sup.4是B可能与A连接；R.sup.1是氢、低碳基或芳基碳基；R.sup.2是氢、低碳基、芳基碳基或酰基；X是烷基]及其盐具有例如对抑制血管紧张素转化酶的活性，并可用作高血压以及心脏病和脑卒中等循环疾病的诊断、预防或治疗剂。
• Piperidine derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04954625A1

  公开（公告）日：1990-09-04

  Novel compounds of the formula: ##STR1## [wherein A is an .alpha.-amino acid residue; B is a group represented by the formula: ##STR2## wherein R.sup.4 is hydrogen, lower alkyl, aralkyl or amino-lower alkyl), whereby the linkage between the symbols A and B designates a peptide bond and the group R.sup.4 in B may be linked with A; R.sup.1 is hydrogen, lower alkyl or aralkyl; R.sup.2 is hydrogen, lower alkyl, aralkyl or acyl; X is alkylene] and salts thereof posses, for example, inhibitory activity on angiotensin converting enzyme, and are useful as an agent for diagnosis, prevention or treatment of hypertension as well as circulatory diseases such as cardiopathy and cerebral apoplexy.

  该公式的新化合物：##STR1## [其中A是α-氨基酸残基；B是由公式表示的基团：##STR2## 其中R.sup.4是氢、低碳基、芳基烷基或氨基-低碳基），其中符号A和B之间的连接表示肽键，基团B中的R.sup.4可以与A连接；R.sup.1是氢、低碳基或芳基烷基；R.sup.2是氢、低碳基、芳基烷基或酰基；X是烷基]及其盐具有例如对血管紧张素转换酶的抑制活性，并且可用作诊断、预防或治疗高血压以及心血管疾病如心脏病和脑卒中的药物。
• US4410520A
  申请人：——

  公开号：US4410520A

  公开（公告）日：1983-10-18
• US4473575A
  申请人：——

  公开号：US4473575A

  公开（公告）日：1984-09-25
• US4575503A
  申请人：——

  公开号：US4575503A

  公开（公告）日：1986-03-11