6-<3-<4-(4-chlorobenzyl)-1-piperazinyl>propoxy><1>benzopyrano<2,3-d>-1,2,3-triazol-9(1H)-one | 79837-61-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-<3-<4-(4-chlorobenzyl)-1-piperazinyl>propoxy><1>benzopyrano<2,3-d>-1,2,3-triazol-9(1H)-one
• 英文别名: 6-{3-[4-(4-chlorobenzyl)-1-piperazinyl]-propoxy}-9-oxo-1H,9H-benzopyrano[2,3-d]-1,2,3-triazole；6-{3-[4-(4-chlorobenzyl)-1-piperazinyl]propoxy}[1]benzopyrano[2,3-d]-1,2,3-triazol-9(1H)-one；6-{3-[4-(4-Chlorobenzyl)-1-piperazinyl]-propoxy}-9-oxo 1H,9H-benzopyrano[2,3-d]-1,2,3-triazole；6-[3-[4-[(4-chlorophenyl)methyl]piperazin-1-yl]propoxy]-2H-chromeno[2,3-d]triazol-9-one
• CAS: 79837-61-9
• 化学式: C₂₃H₂₄ClN₅O₃
• 分子量: 453.928
• InChiKey: YGAHGUFVCXHJQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  83.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-(4-氯苄基)哌嗪 在 potassium carbonate 、 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 丁酮 为溶剂， 反应 27.5h， 生成 6-<3-<4-(4-chlorobenzyl)-1-piperazinyl>propoxy><1>benzopyrano<2,3-d>-1,2,3-triazol-9(1H)-one
  参考文献：
  名称：

  Studies on 1,2,3-triazoles. 13. (Piperazinylalkoxy)-[1]benzopyrano[2,3-d]-1,2,3-triazol-9(1H)-ones with combined H1-antihistamine and mast cell stabilizing properties

  摘要：

  Several N-benzylpiperazino derivatives of [1]benzopyrano[2,3-d]-1,2,3-triazol-9(1H)-one and its 5-methyl homologue have been prepared and evaluated for H1-antihistamine activity on guinea pig ileum. The most potent compounds were also evaluated for their ability to stabilize mast cells in the rat passive peritoneal anaphylaxis (PPA) system and were shown to inhibit histamine release at concentrations below those required to inhibit extravasation, suggesting that this might be relevant to their antianaphylactic activity in this system. The compound tested with the most potent H1-antihistamine activity was 6-[3-[4-(4-chlorobenzyl)-1-piperazinyl]propoxy][1]benzopyrano[2,3- d]-1,2,3-triazol-9(1H)-one, 28, which had a pA2 of 9.1 against histamine on guinea pig ileum, comparable to that of mepyramine, and inhibited histamine release in the rat PPA system with an IC50 value of 5.4 X 10(-6) M.

  DOI：

  10.1021/jm00161a022
• 作为试剂：
  描述：

  5-{3-{3-[4-(4-Chlorobenzyl)-1-piperazinyl]propoxy}phenoxy}-1-(4-methoxybenzyl)-1,2,3-triazole-4-carboxylic acid 、 氯化亚砜 、 三氯化铝 在 N,N-二甲基甲酰胺 氮气 、 氯化亚砜 、 二氯甲烷 、 盐酸 、 水 、 6-<3-<4-(4-chlorobenzyl)-1-piperazinyl>propoxy><1>benzopyrano<2,3-d>-1,2,3-triazol-9(1H)-one 、 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 4.83h， 以gave 2.68 g (35%) of material identical with的产率得到6-<3-<4-(4-chlorobenzyl)-1-piperazinyl>propoxy><1>benzopyrano<2,3-d>-1,2,3-triazol-9(1H)-one
  参考文献：
  名称：

  Process for preparing benzopyrano (2,3-d) triazoles

  摘要：

  一种制备式(I)化合物的方法，其中X为苯基，可选地被一个卤素，C.sub.1-4烷基或C.sub.1-4烷氧基取代；或者为吡啶基；R.sup.1为氢或C.sub.1-6烷基；n为1至6的整数；该方法包括，环化式(II)化合物：其中X、R.sup.1和n与式(I)相关定义相同；Y为羟基或酸活化基团，R.sup.x为氢或N-保护基团，然后如有需要进行以下一项或多项步骤：(i)去除任何保护基R.sup.x，(ii)制备化合物(I)的盐。

  公开号：

  US04692526A1

文献信息

• Synthesis of benzopyranotriazoles
  申请人：BEECHAM GROUP PLC

  公开号：EP0182540A2

  公开（公告）日：1986-05-28

  A process for preparing a compound of formula (I) wherein X is phenyl optionally substituted by one halogen, C1-4 alkyl or Cl-4 alkoxy; or pyridyl; R1 is hydrogen or C1-6 alkyl; and n is an integer of from 1 to 6; which process comprises, cyclising a compound of formula (II) wherein X, R1 and n are as defined in relation to formula (I); Y is an hydroxy or an acid activating group and Rx is hydrogen or an N- protecting group and thereafter if desired carrying out one or more of the following steps: (i) removing any protecting group Rx, (ii) preparing a salt of the compound of formula (I).

  一种制备式(I)化合物的工艺 其中 X 是任选被一个卤素、C1-4 烷基或 Cl-4 烷氧基取代的苯基；或吡啶基；R1 是氢或 C1-6 烷基；n 是 1 至 6 的整数；该工艺包括：将式（II）化合物环化 其中 X、R1 和 n 如式（I）所定义；Y 是羟基或酸活化基团，Rx 是氢或 N-保护基团，然后根据需要进行以下一个或多个步骤：(i) 去除任何保护基团 Rx，(ii) 制备式 (I) 化合物的盐。
• BUCKLE D. R.; ROCKELL C. J. M.; SMITH H.; SPICER B. A., J. MED. CHEM., 29,(1986) N 11, 2262-2267
  作者：BUCKLE D. R.、 ROCKELL C. J. M.、 SMITH H.、 SPICER B. A.

  DOI：——

  日期：——
• US4692526A
  申请人：——

  公开号：US4692526A

  公开（公告）日：1987-09-08
• Process for preparing benzopyrano (2,3-d) triazoles
  申请人：Beecham Group PLC

  公开号：US04692526A1

  公开（公告）日：1987-09-08

  A process for preparing a compound of formula (I) ##STR1## wherein X phenyl optionally substituted by one halogen, C.sub.1-4 alkyl or C.sub.1-4 alkoxy; or pyridyl; R.sup.1 is hydrogen or C.sub.1-6 alkyl; and n is an integer of from 1 to 6; which process comprises, cyclizing a compound of formula (II): ##STR2## wherein X, R.sup.1 and n are as defined in relation to formula (I); Y is an hydroxy or an acid activating group and R.sup.x is hydrogen or an N- protecting group and thereafter if desired carrying out one or more of the following steps: (i) removing any protecting group R.sup.x, (ii) preparing a salt of the compound of formula (I).

  制备式(I)的化合物的过程##STR1##其中X是苯基，可以选择地被一个卤素、C.sub.1-4烷基或C.sub.1-4烷氧基取代；或吡啶基；R.sup.1是氢或C.sub.1-6烷基；n是1到6之间的整数；该过程包括，环化式(II)的化合物：##STR2##其中X、R.sup.1和n如与式(I)相关定义；Y是一个羟基或酸活化基团，R.sup.x是氢或N-保护基团，然后如有必要进行以下一项或多项步骤：(i)去除任何保护基团R.sup.x，(ii)制备式(I)的化合物的盐。
• Studies on 1,2,3-triazoles. 13. (Piperazinylalkoxy)-[1]benzopyrano[2,3-d]-1,2,3-triazol-9(1H)-ones with combined H1-antihistamine and mast cell stabilizing properties
  作者：Derek R. Buckle、Caroline J. M. Rockell、Harry Smith、Barbara A. Spicer

  DOI：10.1021/jm00161a022

  日期：1986.11

  Several N-benzylpiperazino derivatives of [1]benzopyrano[2,3-d]-1,2,3-triazol-9(1H)-one and its 5-methyl homologue have been prepared and evaluated for H1-antihistamine activity on guinea pig ileum. The most potent compounds were also evaluated for their ability to stabilize mast cells in the rat passive peritoneal anaphylaxis (PPA) system and were shown to inhibit histamine release at concentrations below those required to inhibit extravasation, suggesting that this might be relevant to their antianaphylactic activity in this system. The compound tested with the most potent H1-antihistamine activity was 6-[3-[4-(4-chlorobenzyl)-1-piperazinyl]propoxy][1]benzopyrano[2,3- d]-1,2,3-triazol-9(1H)-one, 28, which had a pA2 of 9.1 against histamine on guinea pig ileum, comparable to that of mepyramine, and inhibited histamine release in the rat PPA system with an IC50 value of 5.4 X 10(-6) M.