6-Chloro-3-[3-(1H-imidazol-1-yl)-2-methylpropyl]-1,2,3-benzotriazin-4(3H)-one | 110552-56-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并-1,2,3-三嗪类化合物
• 英文名称: 6-Chloro-3-[3-(1H-imidazol-1-yl)-2-methylpropyl]-1,2,3-benzotriazin-4(3H)-one
• 英文别名: 6-chloro-3-(3-imidazol-1-yl-2-methylpropyl)-1,2,3-benzotriazin-4-one
• CAS: 110552-56-2
• 化学式: C₁₄H₁₄ClN₅O
• 分子量: 303.751
• InChiKey: QMCIFBDOSUSQOT-UHFFFAOYSA-N

物化性质

• 熔点：
  100-102 °C
• 沸点：
  528.2±60.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-Chloro-3-[3-(1H-imidazol-1-yl)-2-methylpropyl]-1,2,3-benzotriazin-4(3H)-one 生成 6-Chloro-3-(3-imidazol-1-yl-2-methylpropyl)-1,2,3-benzotriazin-4-one;hydrochloride
  参考文献：
  名称：

  WRIGHT, WILLIAM BLYTHE (JR);TOMCUFCIK, ANDREW STEPHEN;MARSICO, JOSEPH WIL+

  摘要：

  DOI：
• 作为产物：
  描述：

  2-amino-5-chloro-N-[3-(1 H-imidazol-1-yl)-2-methylpropyl]benzamide 在 盐酸 、 sodium hydroxide 、 sodium nitrite 作用下， 生成 6-Chloro-3-[3-(1H-imidazol-1-yl)-2-methylpropyl]-1,2,3-benzotriazin-4(3H)-one
  参考文献：
  名称：

  Thromboxane synthetase inhibitors and antihypertensive agents. 4. N-[(1H-imidazol-1-yl)alkyl] derivatives of quinazoline-2,4(1H,3H)-diones, quinazolin-4(3H)-ones, and 1,2,3-benzotriazin-4(3H)-ones

  摘要：

  The quinazolinedione, quinazolinone, and 1,2,3-benzotriazinone title compounds were prepared as analogues of N-[(1H-imidazol-1-yl)alkyl]-1H-isoindole-1,3(2H)-diones which were the subject of a previous report from our laboratories. These compounds were evaluated as thromboxane (TX) synthetase inhibitors and as antihypertensive agents. While each series of compounds had activity both as TX synthetase inhibitors and as antihypertensives, the best compounds were N-[(1H-imidazol-1-yl)alkyl]quinazoline-2,4(1H,3H]-diones (V). In general these compounds were all selective enzyme inhibitors at least equipotent with the standard dazoxiben. These compounds were also very active antihypertensive agents as determined in SHR. The SAR is discussed for both types of activity. Compound 20a was further evaluated for TX formation inhibiting properties in several other platelet types both in vitro and ex vivo and is between 100 and 1000 times more potent than dazoxiben.

  DOI：

  10.1021/jm00395a016

文献信息

• 3-heteroalkyl-2,4.quinzaoline-diones
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0293500A1

  公开（公告）日：1988-12-07

  A compound is described which is selected from the group consisting of those of the formula: wherein A is a divalent moiety of the formula: or and n is an integer from 2-10, inclusive; R is hydrogen, oxygen or alkyl having from one to four carbon atoms; Z is C or N; and when Z is N, --- is ――― and there is no R substituent, when Z is C and R is oxygen, --- is ―――; and when Z is C and R is alkyl, --- is ――― ; R6 is hydrogen or alkyl having from one to four carbon atoms; R1 and R2 may be the same or different and may be selected from the group consisting of hydrogen, halogen, trifluoromethyl, alkoxy having from one to four carbon atoms, alkyl having from one to four carbon atoms, nitro and amino; wherein Heteroaryl is wherein R3 and R4 may be selected from hydrogen, alkyl having from one to four carbon atoms, or phenyl; and X is CH or N, together with the pharmaceutically acceptable salts thereof as well as a process for producing the same and its use for pharmaceutical processes.

  描述了一种化合物，所选自以下组合中的一种，其化学式为：其中A是化学式的二价基团：或者n为2-10之间的整数；R为氢、氧或具有1-4个碳原子的烷基；Z为C或N；当Z为N时，---为―――且没有R取代基，当Z为C且R为氧时，---为―――；当Z为C且R为烷基时，---为―――；R6为氢或具有1-4个碳原子的烷基；R1和R2可以相同也可以不同，可选自氢、卤素、三氟甲基、具有1-4个碳原子的烷氧基、具有1-4个碳原子的烷基、硝基和氨基；其中Heteroaryl为其中R3和R4可以选择自氢、具有1-4个碳原子的烷基或苯基；X为CH或N，以及其药学上可接受的盐，以及用于生产该化合物的过程及其在制药过程中的应用。
• 3-imidazolylalkyl-, triazolylalkyl-,
  申请人：American Cyanamid Company

  公开号：US04680293A1

  公开（公告）日：1987-07-14

  Novel 3-heteroarylalkyl-1,2,3-benzotriazin-4(3H)-ones, having the structural formula: ##STR1## wherein A is a divalent moiety of the formula: ##STR2## wherein n is an integer from 3 to 10, inclusive; R.sub.1 and R.sub.2 may be the same or different and may be selected from the group consisting of hydrogen, halogen, trifluoromethyl, alkoxy having from one to four carbon atoms, alkyl having from one to four carbon atoms, nitro and amino; wherein Heteroaryl is ##STR3## wherein R.sub.3 and R.sub.4 may be hydrogen, alkyl having from one to four carbon atoms or phenyl and X is CH or N; together with the pharmaceutically acceptable salts thereof; processes for their preparation and their use in treating prostaglandin-related vascular disorders including ischemic heart disease, transient ischemic attack, thrombosis, migraine and hypertension.

  3-杂环芳基烷基-1,2,3-苯并三唑啉-4(3H)-酮的结构式为：##STR1##其中A是结构式的二价基团：##STR2##其中n是3到10的整数；R.sub.1和R.sub.2可以相同也可以不同，可以选择自氢、卤素、三氟甲基、含有一至四个碳原子的烷氧基、含有一至四个碳原子的烷基、硝基和氨基的基团；其中Heteroaryl是##STR3##其中R.sub.3和R.sub.4可以是氢、含有一至四个碳原子的烷基或苯基，X是CH或N；以及其药用盐；其制备方法及其在治疗前列腺素相关的血管疾病中的用途，包括缺血性心脏病、短暂性缺血性发作、血栓形成、偏头痛和高血压。
• WRIGHT, WILLIAM BLYTHE (JR);TOMCUFCIK, ANDREW STEPHEN;MARSICO, JOSEPH WIL+
  作者：WRIGHT, WILLIAM BLYTHE (JR)、TOMCUFCIK, ANDREW STEPHEN、MARSICO, JOSEPH WIL+

  DOI：——

  日期：——
• US4680293A
  申请人：——

  公开号：US4680293A

  公开（公告）日：1987-07-14
• Thromboxane synthetase inhibitors and antihypertensive agents. 4. N-[(1H-imidazol-1-yl)alkyl] derivatives of quinazoline-2,4(1H,3H)-diones, quinazolin-4(3H)-ones, and 1,2,3-benzotriazin-4(3H)-ones
  作者：William B. Wright、Andrew S. Tomcufcik、Peter S. Chan、Joseph W. Marsico、Jeffery B. Press

  DOI：10.1021/jm00395a016

  日期：1987.12

  The quinazolinedione, quinazolinone, and 1,2,3-benzotriazinone title compounds were prepared as analogues of N-[(1H-imidazol-1-yl)alkyl]-1H-isoindole-1,3(2H)-diones which were the subject of a previous report from our laboratories. These compounds were evaluated as thromboxane (TX) synthetase inhibitors and as antihypertensive agents. While each series of compounds had activity both as TX synthetase inhibitors and as antihypertensives, the best compounds were N-[(1H-imidazol-1-yl)alkyl]quinazoline-2,4(1H,3H]-diones (V). In general these compounds were all selective enzyme inhibitors at least equipotent with the standard dazoxiben. These compounds were also very active antihypertensive agents as determined in SHR. The SAR is discussed for both types of activity. Compound 20a was further evaluated for TX formation inhibiting properties in several other platelet types both in vitro and ex vivo and is between 100 and 1000 times more potent than dazoxiben.