methyl 5-chloro-2-(3-chloromethyl-5-methyl-4H-1,2,4-triazol-4-yl)benzoate | 73268-20-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 5-chloro-2-(3-chloromethyl-5-methyl-4H-1,2,4-triazol-4-yl)benzoate
• 英文别名: 5-chloro-2-[3-(chloromethyl)-5-methyl-4H-1,2,4-triazol-4-yl]benzoic acid methyl ester；methyl 5-chloro-2-[3-(chloromethyl)-5-methyl-1,2,4-triazol-4-yl]benzoate
• CAS: 73268-20-9
• 化学式: C₁₂H₁₁Cl₂N₃O₂
• 分子量: 300.144
• InChiKey: RSPXLTTYBHGRKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  57
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 5-chloro-2-(3-chloromethyl-5-methyl-4H-1,2,4-triazol-4-yl)benzoate 在 tetraphosphorus decasulfide 、 氨 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 20.5h， 生成 8-chloro-4,5-dihydro-1-methyl-6H-s-triazolo<4,3-a><1,4>-benzodiazepin-6-thione
  参考文献：
  名称：

  6-(Substituted-amino)-4H-s-triazolo[4,3-a][1,4]benzodiazepines and 4-(substituted-amino)-6H-s-triazolo[4,3-a][1,4]benzodiazepines with potential antianxiety activity

  摘要：

  A series of 6-(substituted-amino)-4H-s-triazolo[4,3-a][1,4]benzodiazepines was prepared for pharmacological evaluation, and, because of an interesting chemical isomerization, a similar series of 4-(substituted-amino)-6H-s-triazolo[4,3-alpha][1,4]benzodiazepines was also obtained. Pharmacological evaluation of these compounds demonstrated that8-choloro-1-methyl-6-piperidino-4H-s-triazolo[4,3-a][1,4]benzodiazpin e (10) had interesting activity in tests useful for detecting antianxiety activity, while the corresponding 4-piperidino derivative (15) had little activity in these tests. A brief discussion of a possible mechanism for the isomerization is also included.

  DOI：

  10.1021/jm00182a012
• 作为产物：
  描述：

  methyl 5-chloro-2-(3-hydroxymethyl-5-methyl-4H-1,2,4-triazol-4-yl)benzoate 在 氯化亚砜 作用下， 反应 2.6h， 以18.37 g的产率得到methyl 5-chloro-2-(3-chloromethyl-5-methyl-4H-1,2,4-triazol-4-yl)benzoate
  参考文献：
  名称：

  6-(Substituted-amino)-4H-s-triazolo[4,3-a][1,4]benzodiazepines and 4-(substituted-amino)-6H-s-triazolo[4,3-a][1,4]benzodiazepines with potential antianxiety activity

  摘要：

  A series of 6-(substituted-amino)-4H-s-triazolo[4,3-a][1,4]benzodiazepines was prepared for pharmacological evaluation, and, because of an interesting chemical isomerization, a similar series of 4-(substituted-amino)-6H-s-triazolo[4,3-alpha][1,4]benzodiazepines was also obtained. Pharmacological evaluation of these compounds demonstrated that8-choloro-1-methyl-6-piperidino-4H-s-triazolo[4,3-a][1,4]benzodiazpin e (10) had interesting activity in tests useful for detecting antianxiety activity, while the corresponding 4-piperidino derivative (15) had little activity in these tests. A brief discussion of a possible mechanism for the isomerization is also included.

  DOI：

  10.1021/jm00182a012

文献信息

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

  公开号：US04296239A1

  公开（公告）日：1981-10-20

  6-Amino-4H-s-triazolo[4,3-a][1,4]benzodiazepines of the formula ##STR1## wherein R is hydrogen or C.sub.1 to C.sub.3 -alkyl, R.sub.1 is hydrogen or halogen, and the two R.sub.2 groups are taken together with the nitrogen to which they are bonded to complete a nitrogen ring moiety selected from the group consisting of pyrrolidino, piperidino, morpholino and 3,6-dihydro-1(2H)-pyridyl, and the pharmacologically acceptable salts thereof, are central nervous system depressant drugs which are useful in effective dosages in domestic and zoo animals for their calming and tranquilizing uses during shipment and to reduce aggressive behavior. In man these compounds are potentially useful for controlling anxiety and schizophrenia and for their sedative, muscle relaxant and anti-convulsant activity.

  式为##STR1##的6-氨基-4H-s-三唑并[4,3-a][1,4]苯二氮平衍生物，其中R为氢或C.sub.1到C.sub.3-烷基，R.sub.1为氢或卤素，两个R.sub.2基团与它们所连接的氮一起形成从吡咯啉基，哌啶基，吗啉基和3,6-二氢-1(2H)-吡啶基中选择的氮环基团，以及其药理学上可接受的盐，是中枢神经系统抑制剂药物，可在家畜和动物园动物中使用，用于运输期间的镇静和安抚作用以及减少攻击性行为。在人类中，这些化合物潜在地可用于控制焦虑和精神分裂症，以及其镇静，肌肉松弛和抗惊厥活性。
• HESTER J. B. JR.; VOIGTLAENDER P. VON; EVENSON G. N., J. MED. CHEM., 1980, 23, NO 8, 873-877
  作者：HESTER J. B. JR.、 VOIGTLAENDER P. VON、 EVENSON G. N.

  DOI：——

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

  DOI：——

  日期：——
• US4180668A
  申请人：——

  公开号：US4180668A

  公开（公告）日：1979-12-25
• US4296239A
  申请人：——

  公开号：US4296239A

  公开（公告）日：1981-10-20