2-(Dimethylamino)-1,3-dihydro-2H-1,5-benzodiazepin-2-one | 62537-60-4

• 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: 2-(Dimethylamino)-1,3-dihydro-2H-1,5-benzodiazepin-2-one
• 英文别名: 4-(dimethylamino)-1,3-dihydro-2H-1,5-benzodiazepin-2-one；4-(dimetilammino)-1,3-diidro-2H-1,5-benzodiazepine-2-one；4-dimethylamino-1,3-dihydro-benzo[b][1,4]diazepin-2-one；2.3-Dihydro-2-oxo-4-dimethylamino-1H-1.5-benzodiazepin；2H-1,5-Benzodiazepin-2-one, 1,3-dihydro-4-(dimethylamino)-；4-(dimethylamino)-1,3-dihydro-1,5-benzodiazepin-2-one
• CAS: 62537-60-4
• 化学式: C₁₁H₁₃N₃O
• 分子量: 203.244
• InChiKey: SZOFIRPATPUCFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  44.7
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(Dimethylamino)-1,3-dihydro-2H-1,5-benzodiazepin-2-one 在 四氯化钛 、 溶剂黄146 、 苯甲醚 作用下， 以 various solvent(s) 为溶剂， 反应 8.0h， 生成 Methyl-(1-phenyl-4H-2,3,6,10b-tetraaza-benzo[e]azulen-5-yl)-amine
  参考文献：
  名称：

  1,5-Benzodiazepines IX. A new route to substituted 4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepin-5-amines with analgesic and/or anti-inflammatory activities

  摘要：

  A new two-step synthetic pathway to substituted 4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepin-5-amines 2a-p is described. The cyclocondensation of (dimethylamino)benzodiazepinone 1a with hydrazides afforded triazolobenzodiazepinones 5 which in turn reacted with suitable primary or secondary amines, in the presence of titanium tetrachloride, to give the desired 5-amino-derivatives 2a-p. When compounds 5 were treated with the Lawesson's reagent thiolactams 6 were obtained, which then reacted with sodium hydride and proper alkyl halides to yield 5-(alkylthio)derivatives 7a-d. Compounds 2a-h, j-p, and 7a-d were tested for their analgesic and anti-inflammatory activities, as well as for their acute toxicity and gross behavioral effects. The analgesic activity appeared noteworthy in the writhing test, where fifteen compounds were more effective than both the reference drugs acetylsalicylic acid and dipyrone, but was less evident in the hot plate test. An anti-inflammatory activity, lower than that of indomethacin but reaching the level of statistical significance, was displayed in the carrageenin-induced edema assay by five of the nineteen test compounds.

  DOI：

  10.1016/0223-5234(91)90144-c
• 作为产物：
  描述：

  邻苯二胺 、 ethyl 3-(dimethylamino)-3-oxopropanoate 、 三氯氧磷 以21%的产率得到
  参考文献：
  名称：

  ROMA G.; ERMILI A.; BALBI A., FARMACO. ED. SCI., 1977, 32, NO 2, 81-91

  摘要：

  DOI：

文献信息

• 1,5-Benzodiazepines. Part XII. Synthesis and biological evaluation of tricyclic and tetracyclic 1,5-benzodiazepine derivatives as nevirapine analogues
  作者：Mario Di Braccio、Giancarlo Grossi、Giorgio Roma、Laura Vargiu、Massimo Mura、Maria Elena Marongiu

  DOI：10.1016/s0223-5234(01)01283-1

  日期：2001.12

  A number of properly substituted 5H-pyrimido[4,5-b][1,5]benzodiazepines (2) and pyrazolo[3,4-b][1,5]benzodiazepines (3 and 4), as well as compounds 5-7, which are derivatives of new tetracyclic systems, were prepared as nevirapine analogues through multistep synthetic routes. The cytotoxic and anti-HIV-1 properties of compounds 2-7 were evaluated in cell-based assays, together with their inhibitory

  许多适当取代的5H-嘧啶并[4,5-b] [1,5]苯并二氮杂卓（2）和吡唑并[3,4-b] [1,5]苯并二氮杂卓（3和4）以及化合物5 -7是新的四环系统的衍生物，通过多步合成路线制备为奈韦拉平类似物。在基于细胞的测定中评估了化合物2-7的细胞毒性和抗HIV-1特性，并在酶测定中评估了它们对HIV-1重组逆转录酶（rRT）的抑制活性。事实证明，引入奈韦拉平杂环骨架的修饰对抗HIV-1活性具有负面影响。值得注意的是，一些新的衍生物在低微摩尔范围内被证明具有细胞毒性。
• 1,5-Benzodiazepines Part XIII. Substituted 4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepin-5-amines and 4H-imidazo[1,2-a][1,5]benzodiazepin-5-amines as analgesic, anti-inflammatory and/or antipyretic agents with low acute toxicity
  作者：G Grossi

  DOI：10.1016/s0223-5234(02)01400-9

  日期：2002.12.1

  kg(-1) os dose, some compounds 3 and 4 showed notable analgesic or anti-inflammatory activity but no antipyretic properties, whereas the 5-(dibutylamino) derivatives 5b and 5f proved to be significantly endowed with all these activities. Almost all the compounds 3, 4 and 5 did not show acute toxicity in mice up to 800 mg kg(-1) os dose.

  适当的N，N-二烷基-4H- [1,2,4]三唑[4,3-a] [1,5]苯并二氮杂-5-胺（1）与N-氯代琥珀酰亚胺的反应得到其4-氯代衍生物3依次用环胺处理，得到相应的4,5-二氨基衍生物4。N，N-二烷基-4H-咪唑并[1,2-a] [1,5]苯并二氮杂-5-胺（5）为由适合的4-（二烷基氨基）-1,3-二氢-2H-1,5-苯并二氮杂-2--2-酮（8）开始，通过多步合成路线制备。在200 mg kg（-1）os剂量下，某些化合物3和4表现出明显的止痛或抗炎活性，但没有解热特性，而5-（二丁基氨基）衍生物5b和5f被证明具有所有这些活性。 。几乎所有化合物3、4和5在800 mg kg（-1）os剂量的小鼠中均未显示急性毒性。
• Tricyclic diazepine vasopressin antagonists and oxytocin antagonists
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0636625A2

  公开（公告）日：1995-02-01

  Tricyclic diazepines of the formula: wherein A, B, D, E, F, Y and Z are defined in the specification which compounds have vasopressin and oxytocin antagonist activity.

  式中的三环地西泮： 其中 A、B、D、E、F、Y 和 Z 的定义见说明书，这些化合物具有血管加压素和催产素拮抗剂活性。
• Roma; Balbi; Ermili, Farmaco, Edizione Scientifica, 1983, vol. 38, # 8, p. 546 - 558
  作者：Roma、Balbi、Ermili、Vigevani

  DOI：——

  日期：——
• Di Braccio; Roma; Grossi, Il Farmaco, 1992, vol. 47, # 1, p. 77 - 90
  作者：Di Braccio、Roma、Grossi、Leoncini、Maresca

  DOI：——

  日期：——