5-Chloro-3,4-dimethyl-2-nitro-phenylamine | 131885-39-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-Chloro-3,4-dimethyl-2-nitro-phenylamine
• 英文别名: 5-Chloro-3,4-dimethyl-2-nitroaniline
• CAS: 131885-39-7
• 化学式: C₈H₉ClN₂O₂
• 分子量: 200.625
• InChiKey: VFOFNKHYCIPGQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-Chloro-3,4-dimethyl-2-nitro-phenylamine 在 镍 氢气 作用下， 以 甲醇 为溶剂， 25.0~180.0 ℃ 、101.33 kPa 条件下， 反应 34.0h， 生成 5-Imidazol-1-yl-6,7-dimethyl-2-pyridin-4-yl-1H-benzoimidazole
  参考文献：
  名称：

  Cardiotonic agents. Synthesis and cardiovascular properties of novel 2-arylbenzimidazoles and azabenzimidazoles

  摘要：

  Novel 2-arylbenzimidazoles and azabenzimidazoles were synthesized, and their inotropic action was evaluated. Changes in left ventricular pressure, dP/dt max, were measured as an index of cardiac contractility. The structural features that impart optimal inotropic activity are presented. The most potent compounds were evaluated orally in conscious dogs with implanted Konigsberg pressure transducers. To investigate the mechanism of action, the most potent compounds were tested for their calcium-sensitizing properties and their potential for the inhibition of phosphodiesterase. Two compounds, 1 and 4 1, showed interesting in vitro and oral activity without side effects. They have a more potent calcium-sensitizing effect than MCI-154 and are under futher investigation.

  DOI：

  10.1021/jm00101a024
• 作为产物：
  描述：

  N-(2,3-二甲基苯基)乙酰胺 在 盐酸 、 氟硼酸钠 、 氨 、 氯 、 铜 、 sodium nitrite 作用下， 以 乙醇 、 氯仿 、 乙二醇甲醚 、 溶剂黄146 为溶剂， 150.0 ℃ 、3.3 MPa 条件下， 反应 90.0h， 生成 5-Chloro-3,4-dimethyl-2-nitro-phenylamine
  参考文献：
  名称：

  Cardiotonic agents. Synthesis and cardiovascular properties of novel 2-arylbenzimidazoles and azabenzimidazoles

  摘要：

  Novel 2-arylbenzimidazoles and azabenzimidazoles were synthesized, and their inotropic action was evaluated. Changes in left ventricular pressure, dP/dt max, were measured as an index of cardiac contractility. The structural features that impart optimal inotropic activity are presented. The most potent compounds were evaluated orally in conscious dogs with implanted Konigsberg pressure transducers. To investigate the mechanism of action, the most potent compounds were tested for their calcium-sensitizing properties and their potential for the inhibition of phosphodiesterase. Two compounds, 1 and 4 1, showed interesting in vitro and oral activity without side effects. They have a more potent calcium-sensitizing effect than MCI-154 and are under futher investigation.

  DOI：

  10.1021/jm00101a024

文献信息

• RADIOPROTECTOR COMPOUNDS AND METHODS
  申请人：Martin Roger Francis

  公开号：US20130109678A1

  公开（公告）日：2013-05-02

  The invention relates to novel compounds, processes for their preparation and their use in protecting biological materials from radiation damage (radioprotection). Preferred compounds of the invention are those of Formula II, as follows: wherein W represents —N(R 1 R 2 ) where R 1 and R 2 are not both hydrogen and where they may together form a 5, 6 or 7 membered ring structure, —NHN(R 1 R 2 ), —NHR 3 N(R 1 R 2 ), —NHR 3 OR 2 , —N(R 3 )R 3 OR 2 , —N(R 1 )R 3 OR 3 OR 3 , —OR 3 NR 1 R 2 , —OR 3 or W represents piperidyl, piperazinyl, morpholinyl, thiomorpholinyl or diazepanyl each of which may be optionally substituted by C 1 to C 4 alkyl, C 2 to C 4 alkenyl, —N(CO)N(R 1 R 2 ), —N(CO)OR 1 , —N(CO)OR 3 OH, —(CO)NR 1 R 2 , —R 3 (CO)NR 1 R 2 , —R 3 OR 1 , —OR 1 , —N(R 1 R 2 ) or —NH—; R 1 and R 2 are the same or different and are selected from hydrogen, C 1 to C 4 alkyl or C 2 to C 4 alkenyl; R 3 is a C 1 to C 4 alkyl or C 2 to C 4 alkenyl group or chain; Z is the same or different and represents N or CH; Z′ is the same or different and represents N or C; X represents CH, N or NH, where is a double bond when X is CH or N and a single bond when X is NH; X′ represents N or NH, wherein when X is CH or NX′ is NH and wherein X and X′ are different and further where is a double bond when X′ is N and a single bond when X′ is NH; Q represents H, alkoxyl, —NR 1 R 2 , F or Cl; Q 1 is absent when Z′ is N and when Z′ is C it represents H, alkoxyl, —NR 1 R 2 , F or Cl; A represents a five to ten membered single or multiple ring structure with heterocyclic N or O located at the ortho position, said ring including optional double bonds, substitutions and/or other heteroatoms and pharmaceutically acceptable derivatives thereof.

  本发明涉及新化合物、其制备方法及其在保护生物材料免受辐射损伤（辐射防护）方面的用途。本发明的首选化合物是式 II 所示的化合物，其结构如下：其中，W 代表 —N(R1R2)，其中 R1 和 R2 不全为氢，且它们可以一起形成 5、6 或 7 成员环结构，—NHN(R1R2)、—NHR3N(R1R2)、—NHR3OR2、—N(R3)R3OR2、—N(R1)R3OR3OR3、—OR3NR1R2、—OR3 或 W 代表哌啶基、哌嗪基、吗啉基、硫代吗啉基或二氮杂环庚烷基，每个基团可以选择地被 C1 到 C4 烷基、C2 到 C4 烯基、—N(CO)N(R1R2)、—N(CO)OR1、—N(CO)OR3OH、—(CO)NR1R2、—R3(CO)NR1R2、—R3OR1、—OR1、—N(R1R2) 或 —NH— 取代；R1 和 R2 相同或不同，选择自氢、C1 到 C4 烷基或 C2 到 C4 烯基；R3 是 C1 到 C4 烷基或 C2 到 C4 烯基基团或链；Z 相同或不同，代表 N 或 CH；Z′ 相同或不同，代表 N 或 C；X 代表 CH、N 或 NH，其中当 X 是 CH 或 N 时为双键，当 X 是 NH 时为单键；X′ 代表 N 或 NH，其中当 X 是 CH 或 N 时，X′ 为 NH，且 X 和 X′ 不同，进一步地，当 X′ 为 N 时为双键，当 X′ 为 NH 时为单键；Q 代表 H、烷氧基、—NR1R2、F 或 Cl；当 Z′ 为 N 时，Q1 不存在，当 Z′ 为 C 时，Q1 代表 H、烷氧基、—NR1R2、F 或 Cl；A 代表具有杂环 N 或 O 的五到十成员单环或多环结构，该环在邻位位置包括可选的双键、取代基和/或其他杂原子，以及其药学上可接受的衍生物。
• US8999993B2
  申请人：——

  公开号：US8999993B2

  公开（公告）日：2015-04-07
• USRE46943E1
  申请人：——

  公开号：USRE46943E1

  公开（公告）日：2018-07-10
• Cardiotonic agents. Synthesis and cardiovascular properties of novel 2-arylbenzimidazoles and azabenzimidazoles
  作者：Timur Gungor、Andre Fouquet、Jean Marie Teulon、Daniel Provost、Michele Cazes、Alix Cloarec

  DOI：10.1021/jm00101a024

  日期：1992.11

  Novel 2-arylbenzimidazoles and azabenzimidazoles were synthesized, and their inotropic action was evaluated. Changes in left ventricular pressure, dP/dt max, were measured as an index of cardiac contractility. The structural features that impart optimal inotropic activity are presented. The most potent compounds were evaluated orally in conscious dogs with implanted Konigsberg pressure transducers. To investigate the mechanism of action, the most potent compounds were tested for their calcium-sensitizing properties and their potential for the inhibition of phosphodiesterase. Two compounds, 1 and 4 1, showed interesting in vitro and oral activity without side effects. They have a more potent calcium-sensitizing effect than MCI-154 and are under futher investigation.