(E)-3-Dimethylamino-2-[2-(4-methoxy-benzyl)-2H-tetrazol-5-yl]-acrylic acid ethyl ester | 91660-69-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-3-Dimethylamino-2-[2-(4-methoxy-benzyl)-2H-tetrazol-5-yl]-acrylic acid ethyl ester
• 英文别名: Ethyl 3-(dimethylamino)-2-{2-[(4-methoxyphenyl)methyl]-2H-tetrazol-5-yl}prop-2-enoate；ethyl 3-(dimethylamino)-2-[2-[(4-methoxyphenyl)methyl]tetrazol-5-yl]prop-2-enoate
• CAS: 91660-69-4
• 化学式: C₁₆H₂₁N₅O₃
• 分子量: 331.374
• InChiKey: AXZWOACHSQCIOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  82.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-[(E)-2-(4-isopropyl-1,3-thiazol-2-yl)-1-ethenyl]-2-aminopyridine 、 (E)-3-Dimethylamino-2-[2-(4-methoxy-benzyl)-2H-tetrazol-5-yl]-acrylic acid ethyl ester 在 丙酸 作用下， 生成 8-[(E)-2-(4-Isopropyl-thiazol-2-yl)-vinyl]-3-[2-(4-methoxy-benzyl)-2H-tetrazol-5-yl]-pyrido[1,2-a]pyrimidin-4-one
  参考文献：
  名称：

  MexAB-OprM specific efflux pump inhibitors in Pseudomonas aeruginosa. Part 2: achieving activity in vivo through the use of alternative scaffolds

  摘要：

  Problems of low solubility, high serum protein binding, and lack of efficacy in vivo in first generation MexAB-OprM specific efflux pump inhibitors were addressed. Through the use of pharmacophore modelling, the key structural elements for pump inhibition were defined. Use of alternative scaffolds upon which the key elements were arrayed gave second generation leads with greatly improved physical properties and activity in the potentiation of antibacterial quinolones (levofloxacin and sitafloxacin) versus Pseudomonas aeruginosa in vivo. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.07.027
• 作为产物：
  描述：

  N,N-二甲基甲酰胺二甲基缩醛 、 ethyl 2-[2-(4-methoxybenzyl)-2H-1,2,3,4-tetrazol-5-yl]acetate 在 silica gel 、 正己烷 、 乙酸乙酯 作用下， 反应 3.0h， 以to obtain 14 g (48%) of yellow crystals的产率得到(E)-3-Dimethylamino-2-[2-(4-methoxy-benzyl)-2H-tetrazol-5-yl]-acrylic acid ethyl ester
  参考文献：
  名称：

  Medicine for inhibiting drug elimination pump

  摘要：

  预防和/或治疗微生物感染的药物，其活性成分为以下通用式（I）所表示的化合物：其中，R1和R2表示氢原子、卤原子、羟基或类似物，W1表示—CH═CH—、—CH2O—、—CH2CH2—或类似物；R3表示氢原子、卤原子、羟基或氨基；R4表示氢原子、—OZ0-4R5（Z0-4表示烷基、氟代烷基或单键，R5表示环烷基、芳基或类似物）；W2表示单键或—C（R8）═C（R9）—（R8和R9表示氢原子、卤原子、低烷基或类似物，Q表示酸性基团，但W2和Q可以共同形成乙烯基噻唑烷二酮或等效的杂环环；m和n表示0至2的整数，q表示0至3的整数。

  公开号：

  US20050009843A1

文献信息

• Medicine for inhibiting drug elimination pump
  申请人：Nakayama Kiyoshi

  公开号：US20050009843A1

  公开（公告）日：2005-01-13

  A medicament for preventive and/or therapeutic treatment of a microbial infection which comprises as an active ingredient a compound represented by the following general formula (I): wherein, R 1 and R 2 represent hydrogen atom, a halogen atom, hydroxyl group or the like, W 1 represents —CH═CH—, —CH 2 O—, —CH 2 CH 2 — or the like; R 3 represents hydrogen atom, a halogen atom, hydroxyl group or an amino group; R 4 represents hydrogen atom, a group of —OZ 0-4 R 5 (Z 0-4 represents an alkylene group, a fluorine-substituted alkylene group or a single bond, and R 5 represents a cyclic alkyl group, an aryl group or the like); W 2 represents a single bond or —C(R 8 )═C(R 9 )—(R 8 and R 9 represent hydrogen atom, a halogen atom, a lower alkyl group or the like, Q represents an acidic group, but W 2 and Q may together form vinylidenethiazolidinedione or an equivalent heterocyclic ring; m and n represent an integer of 0 to 2, and q represents an integer of 0 to 3.

  预防和/或治疗微生物感染的药物，其活性成分为以下通用式（I）所表示的化合物：其中，R1和R2表示氢原子、卤原子、羟基或类似物，W1表示—CH═CH—、—CH2O—、—CH2CH2—或类似物；R3表示氢原子、卤原子、羟基或氨基；R4表示氢原子、—OZ0-4R5（Z0-4表示烷基、氟代烷基或单键，R5表示环烷基、芳基或类似物）；W2表示单键或—C（R8）═C（R9）—（R8和R9表示氢原子、卤原子、低烷基或类似物，Q表示酸性基团，但W2和Q可以共同形成乙烯基噻唑烷二酮或等效的杂环环；m和n表示0至2的整数，q表示0至3的整数。
• MexAB-OprM specific efflux pump inhibitors in Pseudomonas aeruginosa. Part 2: achieving activity in vivo through the use of alternative scaffolds
  作者：Kiyoshi Nakayama、Yohei Ishida、Masami Ohtsuka、Haruko Kawato、Ken-ichi Yoshida、Yoshihiro Yokomizo、Toshiharu Ohta、Kazuki Hoshino、Tsuyoshi Otani、Yuichi Kurosaka、Kumi Yoshida、Hiroko Ishida、Ving J. Lee、Thomas E. Renau、William J. Watkins

  DOI：10.1016/j.bmcl.2003.07.027

  日期：2003.12

  Problems of low solubility, high serum protein binding, and lack of efficacy in vivo in first generation MexAB-OprM specific efflux pump inhibitors were addressed. Through the use of pharmacophore modelling, the key structural elements for pump inhibition were defined. Use of alternative scaffolds upon which the key elements were arrayed gave second generation leads with greatly improved physical properties and activity in the potentiation of antibacterial quinolones (levofloxacin and sitafloxacin) versus Pseudomonas aeruginosa in vivo. (C) 2003 Elsevier Ltd. All rights reserved.
• Drug efflux pump inhibitor
  申请人：Nakayama Kiyoshi

  公开号：US20060106034A1

  公开（公告）日：2006-05-18

  A medicament for preventive and/or therapeutic treatment of a microbial infection which comprises as an active ingredient a compound represented by the following general formula (I): wherein, R 1 and R 2 represent hydrogen atom, a halogen atom, hydroxyl group or the like, W 1 represents —CH═CH—, —CH 2 O—, —CH 2 CH 2 — or the like; R 3 represents hydrogen atom, a halogen atom, hydroxyl group or an amino group; R 4 represents hydrogen atom, a group of —OZ 0-4 R 5 (Z 0-4 represents an alkylene group, a fluorine-substituted alkylene group or a single bond, and R 5 represents a cyclic alkyl group, an aryl group or the like); W 2 represents a single bond or —C(R 8 )═C(R 9 )−(R 8 and R 9 represent hydrogen atom, a halogen atom, a lower alkyl group or the like, Q represents an acidic group, but W 2 and Q may together form vinylidenethiazolidinedione or an equivalent heterocyclic ring; m and n represent an integer of 0 to 2, and q represents an integer of 0 to 3.

  一种预防和/或治疗微生物感染的药物，其包括以下通式（I）所代表的化合物作为活性成分： 其中，R1和R2代表氢原子、卤素原子、羟基或类似物，W1代表-CH═CH-、-CH2O-、-CH2CH2-或类似物；R3代表氢原子、卤素原子、羟基或氨基；R4代表氢原子、-OZ0-4R5（Z0-4代表烷基、氟代烷基或单键，R5代表环烷基、芳基或类似物）的基团；W2代表单键或-C(R8)═C(R9)-（R8和R9代表氢原子、卤素原子、低烷基或类似物），Q代表酸性基团，但W2和Q可以一起形成乙烯基噻唑烷二酮或等效的杂环环；m和n表示0到2的整数，q表示0到3的整数。