4-[2-(1H-咪唑-1-基)乙氧基]苯甲酰胺 | 75912-57-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-[2-(1H-咪唑-1-基)乙氧基]苯甲酰胺
• 英文名称: 4-<2-(1H-imidazol-1-yl)ethoxy>benzamide
• 英文别名: 1-[2-(4-carbamoylphenoxy)ethyl]imidazole；4-(2-(1H-imidazol-1-yl)ethoxy)benzamide；4-(2-imidazol-1-ylethoxy)benzamide
• CAS: 75912-57-1
• 化学式: C₁₂H₁₃N₃O₂
• 分子量: 231.254
• InChiKey: DVALIYTWWUIPGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[2-(1H-咪唑-1-基)乙氧基]苯甲酰胺 在 sodium azide 、 乙酸酐 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 5-<4-<2-(1H-imidazol-1-yl)ethoxy>phenyl>-1H-tetrazole
  参考文献：
  名称：

  Selective thromboxane synthetase inhibitors. 1. 1-[(Aryloxy)alkyl]-1H-imidazoles

  摘要：

  1-(2-Phenoxyethyl)-1H-imidazole was found to be an inhibitor of thromboxane (TxA2) synthetase, but it also inhibited the adrenal cytochrome P-450 enzyme steroid 11 beta-hydroxylase. The preparation of a series of analogues is described, and activity against TxA2 synthetase, PGI2 synthetase, cyclooxygenase, and steroid 11 beta-hydroxylase is discussed. Potency against TxA2 synthetase was increased by introduction of a carboxyl group at a suitable distance from the imidazole ring. A distance of 8.1-8.8 A between N-1 of the imidazole and the carboxyl carbon was found to be optimal. Introduction of a carboxyl group also had the effect of reducing activity against steroid 11 beta-hydroxylase. The most potent and selective compound was found to be 4-[2-(1H-imidazol-1-yl) ethoxy]benzoic acid (14).

  DOI：

  10.1021/jm00148a009
• 作为产物：
  描述：

  咪唑 、 2-(4-carbamoylphenoxy)-ethyl chloride 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 生成 4-[2-(1H-咪唑-1-基)乙氧基]苯甲酰胺
  参考文献：
  名称：

  N-(phenoxyalkyl)imidazoles as selective inhibitors of the thromboxane

  摘要：

  N-(单取代或双取代苯氧烷基)咪唑及其药用可接受的酸盐能够选择性地抑制血栓素合成酶酶的作用，而不显著抑制前列环素合成酶或环氧化酶酶的作用，因此在缺血性心脏病、中风、短暂性缺血发作、血栓形成、偏头痛以及糖尿病的血管并发症治疗中是有用的。

  公开号：

  US04602016A1

文献信息

• Heterocyclic compounds as ligands of the GABAA receptor
  申请人：——

  公开号：US20030105081A1

  公开（公告）日：2003-06-05

  Disclosed are heterocyclic compounds of the formula 1 and the pharmaceutically acceptable salts thereof wherein the variables A, V, Y, J, E, X, T, G, Q, W, Z, b, n and m are defined herein. These compounds are highly selective agonists, antagonists or inverse agonists for GABA A brain receptors or prodrugs of agonists, antagonists or inverse agonists for GABA A brain receptor.

  揭示了具有以下公式的杂环化合物及其药用可接受的盐，其中变量A、V、Y、J、E、X、T、G、Q、W、Z、b、n和m在此处被定义。这些化合物是GABA A 脑受体的高度选择性激动剂、拮抗剂或逆激动剂，或者是GABA A 脑受体的激动剂、拮抗剂或逆激动剂的前药。
• N-(phenoxyalkyl)imidazoles as selective inhibitors of the thromboxane
  申请人：Pfizer Inc.

  公开号：US04602016A1

  公开（公告）日：1986-07-22

  N-(mono or disubstituted phenoxyalkyl)imidazoles and the pharmaceutically acceptable acid addition salts thereof are able to selectively inhibit the action of the thromboxane synthetase enzyme without significantly inhibiting the action of the prostacycline synthetase or cyclooxygenase enzymes and are thus useful in the treatment of ischaemic heart disease, stroke, transient ischaemic attack, thrombosis, migraine, and the vascular complications of diabetes.

  N-(单取代或双取代苯氧烷基)咪唑及其药用可接受的酸盐能够选择性地抑制血栓素合成酶酶的作用，而不显著抑制前列环素合成酶或环氧化酶酶的作用，因此在缺血性心脏病、中风、短暂性缺血发作、血栓形成、偏头痛以及糖尿病的血管并发症治疗中是有用的。
• AZACYCLIC COMPOUNDS AS INHIBITORS OF SENSORY NEURONE SPECIFIC SODIUM CHANNELS
  申请人：Hamlyn Richard

  公开号：US20100204224A1

  公开（公告）日：2010-08-12

  Compounds of the formula (I), and pharmaceutically acceptable salts thereof, are found to be antagonists of SNS sodium channels. They are therefore useful as analgesic and neuroprotective agents; wherein (1) represents (A), (B) or (C); R 1 represents: (a) -L-A or L′-A′ wherein L represents a bond or a C 1 -C 6 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl moiety, A represents a phenyl, 5- to 10-membered heteroaryl, C 3 -C 6 carbocyclyl or 5- to 10 membered heterocyclyl group, L′ represents a C 1 -C 6 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl moiety, and A′ represents -Het-A or —X-A wherein Het represents —O—, —S— or NR′, and X represents —CO—, —SO—, SO 2 —, —CO—O—, CO—S, CONR′, —O—CO—, —S—CO— or NR′—CO—, wherein R′ represents hydrogen or C 1 -C 6 alkyl; (b) -L-A-A′ or -L-A-L-A wherein A′ is as defined above, each A is the same or different and is as defined above and each L is the same or different and is as defined above; (c) -A-Z-A wherein Z is -Het-L′, —X-L′, -L′-Het- or L′-X, wherein Het, L′ and X are as defined above and each A is the same or different and is as defined above; (d) -A-Het-Y or -A-X—Y wherein is [L′-Het] n -L′, [L′-Het] n -L′, -[L′-Het] n -A, -L′-B-L′, -L′-B-A or -A-L-A wherein n is from 1 to 4 and B is —X—, —NR′—CO—NR′, —O—CO—NR′— or —NR′—CO—O, and wherein X and L are as defined above, each A is the same or different and is as defined above, each L′ is the same or different and is as defined above, each R′ is the same or different and is as defined above and each Het is the same or different and is as defined above; or (e) -L-CR(A)(A′) or L-CR(A)(L-A) wherein R is hydrogen or C 1 -C 4 alkyl, A′ is as defined above, each L is the same or different and is as defined above and each A is the same or different and is as defined above; R 2 represents -L-A-, L′-A′, -L-A-A′ or L-A-L-A wherein L′ and A′ are as defined above, each L is the same or different and is as defined above and each A is the same or different and is as defined above J represents —NR 3 —, —O— or a direct bond wherein R 3 represent s hydrogen C 1 -C 6 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl; p is an integer from 1 to 3; q is 1 or 2; and one of E and E′ is —CH 2 — and the other is a direct bond.

  式(I)的化合物及其药学上可接受的盐被发现是SNS钠通道的拮抗剂。它们因此可作为镇痛和神经保护剂使用；其中(1)代表(A)、(B)或(C)；R1代表：(a) -L-A或L'-A'，其中L代表一个键或一个C1-C6烷基，C2-C6烯基或C2-C6炔基基团，A代表一个苯基，5-至10-成员杂芳基，C3-C6环烷基或5-至10-成员杂环基团，L'代表一个C1-C6烷基，C2-C6烯基或C2-C6炔基基团，A'代表-Het-A或-X-A，其中Het代表-O-、-S-或NR'，X代表-CO-、-SO-、SO2-、-CO-O-、CO-S、CONR'、-O-CO-、-S-CO-或NR'-CO-，其中R'代表氢或C1-C6烷基；(b) -L-A-A'或-L-A-L-A，其中A'如上所定义，每个A相同或不同，如上所定义，每个L相同或不同，如上所定义；(c) -A-Z-A，其中Z为-Het-L'、-X-L'、-L'-Het-或L'-X，其中Het、L'和X如上所定义，每个A相同或不同，如上所定义；(d) -A-Het-Y或-A-X-Y，其中是[L'-Het]n-L'、[L'-Het]n-L'、-[L'-Het]n-A、-L'-B-L'、-L'-B-A或-A-L-A，其中n为1至4，B为-X-、-NR'-CO-NR'-、-O-CO-NR'-或-NR'-CO-O，其中X和L如上所定义，每个A相同或不同，如上所定义，每个L'相同或不同，如上所定义，每个R'相同或不同，如上所定义，每个Het相同或不同，如上所定义；或(e) -L-CR(A)(A')或L-CR(A)(L-A)，其中R为氢或C1-C4烷基，A'如上所定义，每个L相同或不同，如上所定义，每个A相同或不同，如上所定义；R2代表-L-A-、L'-A'、-L-A-A'或L-A-L-A，其中L'和A'如上所定义，每个L相同或不同，如上所定义，每个A相同或不同，如上所定义；J代表-NR3-、-O-或直接键，其中R3代表氢、C1-C6烷基、C2-C6烯基或C2-C6炔基；p为1至3的整数；q为1或2；E和E'中的一个为-CH2-，另一个为直接键。
• CROSS, P. E.;DICKINSON, R. P.;PARRY, M. J.;RANDALL, M. J., J. MED. CHEM., 1985, 28, N 10, 1427-1432
  作者：CROSS, P. E.、DICKINSON, R. P.、PARRY, M. J.、RANDALL, M. J.

  DOI：——

  日期：——
• HETEROCYCLIC COMPOUNDS AS LIGANDS OF THE GABA A? RECEPTOR
  申请人：NEUROGEN CORPORATION

  公开号：EP1325006A2

  公开（公告）日：2003-07-09