5-(2-氯苯基)-1,3-二氢-1,4-苯并二氮杂-2-硫酮 | 39061-98-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 中文名称: 5-(2-氯苯基)-1,3-二氢-1,4-苯并二氮杂-2-硫酮
• 英文名称: 1,3-Dihydro-5-(o-chlorphenyl)-2H-1,4-benzodiazepin-2-thion
• 英文别名: 5-(2-chloro-phenyl)-1,3-dihydro-benzo[e][1,4]diazepine-2-thione；1,3-dihydro-5-(o-chlorophenyl)-2H-1,4-benzodiazepine-2-thione；5-(2-chlorophenyl)-1,3-dihydro-1,4-benzodiazepine-2-thione
• CAS: 39061-98-8
• 化学式: C₁₅H₁₁ClN₂S
• 分子量: 286.785
• InChiKey: YBONEDOZZPSNOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 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：
  56.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(2-氯苯基)-1,3-二氢-1,4-苯并二氮杂-2-硫酮 在 N2 作用下， 以 水 、 正丁醇 为溶剂， 生成 U 35005
  参考文献：
  名称：

  6-(O-Halophenyl)-1-methyl-4H-s-triazolo[4,3-a][1,4]-benzodiazepine

  摘要：

  以下化学式的6-(o-卤苯基)-1-甲基-4H-s-三唑[4,3-a][1,4]-苯二氮杂环己烷类化合物：##STR1##其中取代基"Hal"是具有原子序数高达35的卤素之一，即氟、氯或溴，以及它们的药理学上可接受的酸盐，特别适用于肌肉松弛和抗焦虑药物。

  公开号：

  US04018788A1
• 作为产物：
  描述：

  1,3-二氢-5-(2-氯苯基)-2H-1,4-苯并二氮杂卓-2-酮 在 劳森试剂 作用下， 以 乙二醇二甲醚 为溶剂， 生成 5-(2-氯苯基)-1,3-二氢-1,4-苯并二氮杂-2-硫酮
  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

• [3-Substituted-5-[(di-methylamino)methyl]-4H-1,2,4-triazol-
  申请人：The Upjohn Company

  公开号：US04010177A1

  公开（公告）日：1977-03-01

  Compounds of the formula I: ##STR1## wherein R.sub.1 is hydroxymethyl, or -CH.sub.2 NR.sub.6 R.sub.7, in which R.sub.6 is -CH.sub.2 -C.tbd.CH, -CH.sub.2 -CH=CH.sub.2, ##STR2## or alkyl of 1 to 3 carbon atoms, inclusive; R.sub.7 is hydrogen or alkyl of 1 to 3 carbon atoms, or together ##STR3## is pyrrolidino, piperidino or morpholino; wherein R.sub.2 is hydrogen, chlorine or fluorine; wherein R.sub.3 is hydrogen, or fluorine if R.sub.2 is fluorine; wherein R.sub.4 is hydrogen, fluorine, chlorine, bromine, nitro, or trifluoromethyl; and wherein R.sub.5 is hydrogen, methyl or ethyl. These compounds, except those in which R.sub.7 is hydrogen, are produced by heating a compound of formula II: ##STR4## wherein R.sub.2, R.sub.3, R.sub.4, and R.sub.5 are defined as hereinabove, and wherein R'.sub.1 is the same as R.sub.1 except that in defining R'.sub.1,R.sub.7 may not be hydrogen, with aqueous formaldehyde in formic acid solution at reflux temperature (about 100.degree. C.). Compounds in which R.sub.7 are hydrogen require steps further shown in the specification. The compounds of formula I and their pharmacologically acceptable acid addition salts thereof have tranquilizing, anti-anxiety and anti-convulsant activity useful for the treatment of animals and man.

  公式I的化合物：##STR1## 其中R.sub.1是羟甲基或-CH.sub.2 NR.sub.6 R.sub.7，其中R.sub.6是-CH.sub.2 -C.tbd.CH，-CH.sub.2 -CH=CH.sub.2，##STR2##或包括1至3个碳原子的烷基; R.sub.7是氢或包括哒啶基，哌啶基或吗啡啶基; R.sub.2是氢，氯或氟; R.sub.3是氢，如果R.sub.2为氟，则为氟; R.sub.4是氢，氟，氯，溴，硝基或三氟甲基; R.sub.5是氢，甲基或乙基。除了R.sub.7为氢的化合物外，这些化合物是通过将公式II的化合物加热而产生的：##STR4##其中R.sub.2，R.sub.3，R.sub.4和R.sub.5的定义如上所述，而R'.sub.1与R.sub.1相同，但在定义R'.sub.1时，R.sub.7可能不是氢，在甲酸溶液中以回流温度（约100°C）与水甲醛反应。其中R.sub.7为氢的化合物需要在规范中进一步步骤。公式I的化合物及其药理学上可接受的酸加盐具有镇静，抗焦虑和抗惊厥活性，可用于动物和人的治疗。
• 1-(2-Aminoethyl)-6-aryl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepines with diuretic and natriuretic activity
  作者：Jackson B. Hester、James H. Ludens、D. Edward Emmert、Bruce E. West

  DOI：10.1021/jm00126a003

  日期：1989.6

  A series of 1-(2-amino-1-phenylethyl)-6-phenyl-4H- [1,2,4]triazolo[4,3-a][1,4]benzodiazepines was prepared and evaluated for diuretic activity. These compounds have diuretic and natriuretic activity but no kaliuretic activity when evaluated by oral administration to the conscious rat. The structure requirements for this activity are discussed. In particular it was found that the 2-aminoethyl side chain at C-1 with hydrogen or methyl substituents on the amino group was required for diuretic activity. A substituent at C-8 was also required; soft substituents such as methylthio and iodo at this position favored activity. Compounds with both phenyl and 2-pyridyl substituents at C-6 were active; substituents on the C-6 phenyl, however, reduced or eliminated the activity. Substituents other than phenyl at the 1-position of the 2-aminoethyl side chain were detrimental to activity; phenyl substitution at this position was required for activity when the substituent at C-8 was chloro but not when it was bromo.
• MOFFETT R. B.; KAMDAR B. V., J. HETEROCYCL. CHEM., 1979, 16, NO 4, 793-797
  作者：MOFFETT R. B.、 KAMDAR B. V.

  DOI：——

  日期：——
• HESTER, J. B. ,, JR.
  作者：HESTER, J. B. ,, JR.

  DOI：——

  日期：——
• US3992408A
  申请人：——

  公开号：US3992408A

  公开（公告）日：1976-11-16