7-nitro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepine-2-thione | 35628-44-5

• 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-phenyl-2H-1,4-benzodiazepine-2-thione
• 英文别名: 7-nitro-5-phenyl-3H-1,4-benzodiazepine-2(1H)-thione；7-nitro-5-phenyl-1,3-dihydro-benzo[e][1,4]diazepine-2-thione；1,3-dihydro-5-phenyl-7-nitro-2H-1,4-benzodiazepin-2-thione；1,3-Dihydro-5-phenyl-7-nitro-2H-1,4-benzodiazepin-2-thion；7-Nitro-5-phenyl-1.3-dihydro-2H-1.4-benzodiazepin-2-thion；2,3-Dihydro-7-nitro-5-phenyl-1H-1,4-benzodiazepine-2-thione；7-nitro-5-phenyl-1,3-dihydro-1,4-benzodiazepine-2-thione
• CAS: 35628-44-5
• 化学式: C₁₅H₁₁N₃O₂S
• 分子量: 297.337
• InChiKey: GEAUJEFXEUWJQP-UHFFFAOYSA-N

物化性质

• 沸点：
  448.8±55.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 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-phenyl-2H-1,4-benzodiazepine-2-thione 在 聚合甲醛 、 硫酸 、 一水合肼 、 溶剂黄146 作用下， 以 乙醇 、 乙腈 为溶剂， 生成 8-Nitro-1-[(dimethylamino)methyl]-6-phenyl-4H-imidazo[1,2-a][ 1,4]benzodiazepine
  参考文献：
  名称：

  Phthalimido alkanone, ethylene ketals

  摘要：

  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。

  公开号：

  US03992408A1
• 作为产物：
  描述：

  硝西泮 在 tetraphosphorus decasulfide 、 碳酸氢钠 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 7-nitro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepine-2-thione
  参考文献：
  名称：

  1,4-苯二氮杂N-亚硝基脒与甲苯磺酰甲基异氰化物的反应：咪达唑仑的新合成

  摘要：

  描述了用作亚胺酰氯的合成等效物的 1,4-苯二氮杂 N-亚硝基脒与甲苯磺酰基甲基异氰化物的单阴离子的反应。该方法得到 3-(4-甲苯磺酰基)咪唑并[1,5-a][1,4]苯二氮卓类化合物，这些化合物尚未在文献中描述。这些系统可以通过咪唑环的烷基化或酰化衍生为相应的三取代的 1,4-苯并二氮杂卓。这些新的杂环衍生物在药物化学领域具有潜在的用途。此外，咪达唑仑 3 具有良好的麻醉特性，可通过化合物 7a 的脱磺酰化一步轻松制备。

  DOI：

  10.1055/s-2004-831243

文献信息

• 6-Phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines
  申请人：The Upjohn Company

  公开号：US03987052A1

  公开（公告）日：1976-10-19

  6-Phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines of the formula (IV): ##SPC1## wherein R is selected from the group consisting of hydrogen, alkyl of 1 to 3 carbon atoms, inclusive, phenyl, benzyl and -COOR' in which R' is alkyl of 1 to 4 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): ##SPC2## 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: ##EQU1## wherein R is defined as above. The new products of formula IV including their pharmacologically acceptable acid addition salts are useful as sedatives, tranquilizers and muscle relaxants in mammals and birds.

  6-苯基-4H-s-三唑并[4,3-a][1,4]苯二氮杂环己烷的化学式（IV）：##SPC1##其中R选自由氢、1至3个碳原子的烷基、苯基、苄基和-COOR'的群，其中R'是1至4个碳原子的烷基；其中R.sub.1选自由氢和1至3个碳原子的烷基；其中R.sub.2、R.sub.3、R.sub.4和R.sub.5选自由氢、1至3个碳原子的烷基、卤素、硝基、氰基、三氟甲基和烷氧基、烷硫基、烷基亚硫基、烷基磺基、烷酰胺基和二烷基胺基，其中碳链基团为1至3个碳原子，通过将化学式（I）的1,3-二氢-5-苯基-2H-1,4-苯二氮杂环己烷-2-硫酮与化学式的有机酸酰肼缩合而制备：##SPC2##其中R.sub.1、R.sub.2、R.sub.3、R.sub.4和R.sub.5如上所定义，与化学式的有机酸酰肼缩合：##EQU1##其中R如上所定义。公式IV的新产品及其药理学上可接受的酸盐在哺乳动物和鸟类中作为镇静剂、安定剂和肌肉松弛剂具有用途。
• 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。
• Hydroxymethylimidazodiazepines and their esters
  申请人：Hoffman-La Roche Inc.

  公开号：US06174881B1

  公开（公告）日：2001-01-16

  The invention is concerned with hydroxymethyl-imidazodiazepines and their esters of general formula I. These compounds can be used as anxiolytic and/or anticonvulsant and/or muscle relaxant and/or sedative-hypnotic active substances.

  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。
• 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。
• 2-Substituted thio-1,4-benzodiazepine derivatives
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US04094870A1

  公开（公告）日：1978-06-13

  2-substituted thio-1,4-benzodiazepine derivatives having medicinal use of the general formula ##STR1## wherein R.sub.1 and R.sub.2 individually signify hydrogen atom or a halogen atom, or a nitro, amino, hydroxy, cyano, alkyl, haloalkyl, alkoxy, alkylthio, alkanesulfinyl, alkanesulfonyl, alkanoylamino or dialkylamino group, R.sub.3 signifies an alkylene group, and R.sub.4 and R.sub.5 individually signify hydrogen atom or an alkyl group and, when R.sub.4 and R.sub.5 are both alkyl groups, said alkyl groups together may form a ring with or without oxygen atom or an imino group, said ring optionally having a substituent or substituents, and its non-toxic pharmaceutically acceptable salts.

  具有药用价值的2-取代硫代-1,4-苯二氮平衍生物的一般式如下：##STR1## 其中，R.sub.1和R.sub.2分别表示氢原子或卤素原子，或者是硝基、氨基、羟基、氰基、烷基、卤代烷基、烷氧基、烷硫基、烷基磺酰基、烷基磺酰胺基或二烷基氨基基团；R.sub.3表示烷基；R.sub.4和R.sub.5分别表示氢原子或烷基团，当R.sub.4和R.sub.5均为烷基团时，所述烷基团可以与或不与氧原子或亚氨基团一起形成环，所述环可以有取代基或取代基，以及其无毒的药学上可接受的盐。