7-nitro-1,3-dihydro-5-(2-chlorophenyl)-2H-1,4-benzodiazepine-2-thione | 35628-48-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: 7-nitro-1,3-dihydro-5-(2-chlorophenyl)-2H-1,4-benzodiazepine-2-thione
• 英文别名: 5-(2-chlorophenyl)-7-nitro-3H-1,4-benzodiazepine-2(1H)-thione；5-(2-chloro-phenyl)-7-nitro-1,3-dihydro-benzo[e][1,4]diazepine-2-thione；5-(2-chlorophenyl)-7-nitro-1,3-dihydro-2H-1,4-benzodiazepine-2-thione；7-nitro-1,3-dihydro-5-(o-chlorophenyl)-2H-1,4-benzodiazepine-2-thione；1,3-Dihydro-5-(o-chlorphenyl)-7-nitro-2H-1,4-benzodiazepin-2-thion；1,3-dihydro-7-nitro-5-(o-chlorophenyl)-2H-1,4-benzodiazepine-2-thione；5-(2-chlorophenyl)-7-nitro-1,3-dihydro-1,4-benzodiazepine-2-thione
• CAS: 35628-48-9
• 化学式: C₁₅H₁₀ClN₃O₂S
• 分子量: 331.782
• InChiKey: IZYKFSZYKIUTTE-UHFFFAOYSA-N

物化性质

• 沸点：
  476.9±55.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)
• 溶解度：
  溶于二甲基甲酰胺

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-nitro-1,3-dihydro-5-(2-chlorophenyl)-2H-1,4-benzodiazepine-2-thione 在 ammonium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 2-amino-5-(2-chlorophenyl)-7-nitro-3H-1,4-benzodiazepine
  参考文献：
  名称：

  Hydroxymethylimidazodiazepines and their esters

  摘要：

  这项发明涉及羟甲基咪唑二氮杂环己酮及其一般式I的酯类化合物。这些化合物可用作抗焦虑、抗癫痫、肌肉松弛和催眠-催眠活性物质。

  公开号：

  US06174881B1
• 作为产物：
  描述：

  5-(邻氯苯基)-1,3-二氢-7-硝基-2H-1,4-苯并二氮杂草-2-酮 在 劳森试剂 作用下， 以 乙二醇二甲醚 为溶剂， 生成 7-nitro-1,3-dihydro-5-(2-chlorophenyl)-2H-1,4-benzodiazepine-2-thione
  参考文献：
  名称：

  Pyrazolobenzodiazepines: Part I. Synthesis and SAR of a potent class of kinase inhibitors

  摘要：

  A novel series of pyrazolobenzodiazepines 3 has been identified as potent inhibitors of cyclin-dependent kinase 2 (CDK2). Their synthesis and structure-activity relationships (SAR) are described. Representative compounds from this class reversibly inhibit CDK2 activity in vitro, and block cell cycle progression in human tumor cell lines. Further exploration has revealed that this class of compounds inhibits several kinases that play critical roles in cancer cell growth and division as well as tumor angiogenesis. Together, these properties suggest a compelling basis for their use as antitumor agents. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.079

文献信息

• Neurotropic and psychotropic agents. IV. Synthesis and pharmacological properties of 7-chloro-5-(2-chlorophenyl)-2-(2-dimethylaminoethylthio)-3H-1,4-benzodiazepine and related compounds.
  作者：MASAAKI MATSUO、KIYOSHI TANIGUCHI、IKUO UEDA

  DOI：10.1248/cpb.30.1141

  日期：——

  The synthesis and pharmacological properties of 7-chloro-5-(2-chlorophenyl)-2-(2-dimethylaminoethylthio)-3H-1, 4-benzodiazepine (III-1) and related compounds are described. Compound III-1 was prepared from the thiolactam (II-1) by treatment with 2-dimethylaminoethyl chloride in the presence of base in aqueous methanol and 7-chloro-5-(2-ohlorophenyl)-2-methoxy-3H-1, 4-benzodiazepine (IV) was obtained as a by-product. The latter (IV) was hydrolyzed in acid medium to give methyl (E)-[2-amino-5-chloro-α-(2-chlorophenyl) benzylidene] aminoacetate (syn-form) (XIX), which was converted into the 1, 4-benzodiazepine (I-1) by further acid treatment. Compound XIX isomerized to the corresponding anti-form (XXII) on heating. Most of the compounds prepared had an effect similar to that of diazepam in causing taming and anticonvulsant effects in mice.

  描述了7-氯-5-(2-氯苯基)-2-(2-二甲氨基乙基硫)-3H-1, 4-苯二氮卓（III-1）及相关化合物的合成和药理特性。化合物III-1是通过将硫内酰胺（II-1）与2-二甲氨基乙基氯在碱性水甲醇条件下反应而制备的，同时获得了副产物7-氯-5-(2-氯苯基)-2-甲氧基-3H-1, 4-苯二氮卓（IV）。后者（IV）在酸性介质中水解，生成甲基（E）-[2-氨基-5-氯-α-(2-氯苯基)苯乙烯]氨基乙酸酯（顺式）(XIX)，该化合物经过进一步的酸处理转化为1, 4-苯二氮卓（I-1）。化合物XIX在加热时异构化为相应的反式（XXII）。大多数合成的化合物在小鼠中表现出类似于地西泮的抚慰和抗惊厥效果。
• Phthalimido alkanone, ethylene ketals
  申请人：The Upjohn Company

  公开号：US03992408A1

  公开（公告）日：1976-11-16

  Phthalimides of the Formula ##SPC1## Wherein X is NH.sub.2, N(CH.sub.3).sub.2, Cl or Br and R.sub.0 and R.sub.1 are hydrogen, methyl or ethyl are disclosed as intermediates in the preparation of benzodiazepines.

  式为##SPC1##的邻苯二甲酰亚胺是苯二氮杂环己烷类药物的制备中间体，其中X为NH.sub.2、N(CH.sub.3).sub.2、Cl或Br，R.sub.0和R.sub.1为氢、甲基或乙基。
• Carbamoyloxyamino-1,4-benzodiazepines and medicaments containing these
  申请人：Hoechst Aktiengesellschaft

  公开号：US04395409A1

  公开（公告）日：1983-07-26

  What are disclosed are 1,4-benzodiazepines, having a carbamoyloxyamino group, of the following formula I ##STR1## tautomers thereof of the following formula IA ##STR2## physiologically tolerated salts thereof, said compounds having an anxiolytic action without sedating, a process for the preparation of these new compounds, pharmaceutical agents which contain the active compounds, and methods for treating anxiety states with said compounds.

  披露的是具有以下化学式I的具有羰胺氧基氨基基团的1,4-苯二氮䓬类化合物，其互变异构体具有以下化学式IA，其生理耐受盐，这些化合物具有抗焦虑作用但不具有镇静作用，以及制备这些新化合物的方法，含有活性化合物的药物制剂，以及使用这些化合物治疗焦虑状态的方法。
• Triazolo-benzodiazepines
  申请人：The Upjohn Company

  公开号：US04902794A1

  公开（公告）日：1990-02-20

  1-Substituted-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines of the formula (III): ##STR1## wherein R is selected from the group consisting of hydroxy, esters thereof, and alkoxy, in which the alkyl group is of 1 to 3 carbon atoms, inclusive; wherein R.sub.1 is selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms, inclusive; and wherein R.sub.2, R.sub.3, R.sub.4, and R.sub.5 are selected from the group consisting of hydrogen, alkyl of 1 to 3 carbon atoms, inclusive, halogen, nitro, cyano, trifluoromethyl, and alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkanoylamino, and dialkylamino in which the carbon chain moieties are of 1 to 3 carbon atoms, inclusive, are produced by condensing a 1,3-dihydro-5-phenyl-2H-1,4-benzodiazepine-2-thione of the formula (I): ##STR2## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, and R.sub.5 are defined as above, with an organic acid hydrazide of the formula (II): ##STR3## wherein R' is selected from the group consisting of hydroxy, and alkoxy defined as above. When R' is hydroxy, esters can be made in conventional manner. The new products of formula III including their pharmacologically acceptable acid addition salts and N-oxides are useful as sedatives, tranquilizers and muscle relaxants in mammals and birds.

  公式（III）的1-取代-6-苯基-4H-s-三唑并[4,3-a][1,4]苯二氮平，其中R选择从羟基，其酯和烷氧基的群体中选择，其中烷基的碳原子为1到3个，包括；其中R1选择从氢和1到3个碳原子的烷基的群体中选择；其中R2，R3，R4和R5选择从羟基，1到3个碳原子的烷基，卤素，硝基，氰基，三氟甲基和烷氧基，烷基硫醚，烷基亚磺酰，烷基磺酰，烷酰胺和双烷基氨基中选择，其中碳链基团为1到3个碳原子，包括；通过将公式（I）的1,3-二氢-5-苯基-2H-1,4-苯二氮平-2-硫酮与公式（II）的有机酸腙缩合而制备。其中，R1，R2，R3，R4和R5如上所定义，R'选择从羟基和如上定义的烷氧基中选择。当R'为羟基时，酯可以以常规方式制备。公式III的新产品包括其药理学上可接受的酸盐和N-氧化物，可用作哺乳动物和鸟类的镇静剂，安定剂和肌肉松弛剂。
• 1-(Aminoalkyl)
  申请人：The Upjohn Company

  公开号：US04250094A1

  公开（公告）日：1981-02-10

  1-(Aminoalkyl) substituted-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines of the formula II: ##STR1## wherein R.sub.0 is selected from the group consisting of hydrogen, methyl, or ethyl; wherein R' and R" are selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms, inclusive; wherein R.sub.1 is selected from the group consisting of hydrogen, alkyl as defined above; wherein R.sub.2, R.sub.3, R.sub.4, and R.sub.5 are selected from the group consisting of hydrogen, alkyl as defined above, halogen, nitro, cyano, trifluoromethyl, and alkoxy, alkylthio, alkylsulfinyl, and alkylsulfonyl, in which the carbon chain moieties are of 1 to 3 carbon atoms, inclusive, are prepared by reacting a compound of the formula: ##STR2## wherein X is chlorine or bromine and wherein R.sub.0, R.sub.1, R.sub.2, R.sub.3, R.sub.4, and R.sub.5 are defined as above with an amine of the formula: ##STR3## wherein R' and R" are defined as above. The new products of formula II including their pharmacologically acceptable acid addition salts and N-oxides are useful as sedatives, tranquilizers, muscle relaxants and antidepressants in mammals and birds.

  式II中的1-(氨基烷基)取代-6-苯基-4H-s-三唑并[4,3-a][1,4]苯二氮平，其中R.sub.0从氢、甲基或乙基中选择；其中R'和R"从氢和1到3个碳原子的烷基中选择；其中R.sub.1从氢和上述定义的烷基中选择；其中R.sub.2、R.sub.3、R.sub.4和R.sub.5从氢、上述定义的烷基、卤素、硝基、氰基、三氟甲基、烷氧基、烷硫基、烷基亚磺酰基中选择，其中碳链基团为1到3个碳原子，包括通过将式中R.sub.0、R.sub.1、R.sub.2、R.sub.3、R.sub.4和R.sub.5定义为上述的化合物与式为： ##STR2## 其中X为氯或溴，R.sub.0、R.sub.1、R.sub.2、R.sub.3、R.sub.4和R.sub.5如上所定义，与式为： ##STR3## 其中R'和R"如上所定义的胺反应制备而成。式II的新产品，包括其药理学上可接受的酸盐和N-氧化物，可用作哺乳动物和鸟类的镇静剂、安定剂、肌肉松弛剂和抗抑郁剂。