7-咪唑-1-基萘-2-羧酸 | 95355-07-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 7-咪唑-1-基萘-2-羧酸
• 英文名称: 7-(1H-imidazol-1-yl)-2-naphthalenecarboxylic acid
• 英文别名: 2-(1-imidazolyl)-7-carboxynaphthalene；2-Naphthalenecarboxylic acid, 7-(1H-imidazol-1-yl)-；7-imidazol-1-ylnaphthalene-2-carboxylic acid
• CAS: 95355-07-0
• 化学式: C₁₄H₁₀N₂O₂
• 分子量: 238.246
• InChiKey: VTUOCDJOZKEHHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933290090

反应信息

• 作为产物：
  描述：

  7-(1H-咪唑-1-基)-5,6-二氢-2-萘甲酸 在 氢氧化钾 、 氯化亚砜 、 sulfur 作用下， 反应 32.0h， 生成 7-咪唑-1-基萘-2-羧酸
  参考文献：
  名称：

  N-imidazolyl derivatives of the napththalene and chroman rings as thromboxane A2 synthase inhibitors

  摘要：

  A series of N-imidazol-1-yl derivatives of 1,2-dihydronaphthalene, 1,2,3,4-tetrahydronaphthalene, 2H-1-benzopyran and some related compounds were synthesized and tested as inhibitors of thromboxane A2 synthase in ex vivo experiments with orally treated rats. Some compounds showed good activity which was confirmed in experiments in vitro in rabbit whole blood. Some structural requirements for significant TxA2 synthase inhibitory activity are discussed. The selected 5,6-Dihydro-7-(H-1-imidazol-1-yl)-2-naphthalene-carboxylic acid (compound 7) was conformationally analysed using the Sybyl molecular model system in comparison with dazoxiben. Compound 7 was further pharmacologically investigated and on the basis of its interesting activities in vitro, ex vivo and in vivo and its low toxicity was selected for clinical investigation.

  DOI：

  10.1016/0223-5234(91)90103-t

文献信息

• COMBINED USE OF N-IMIDAZOLYL DERIVATIVES OF BICYCLIC COMPOUNDS AND CYCLOSPORINE IN THERAPY
  申请人：FARMITALIA CARLO ERBA S.r.l.

  公开号：EP0433427A1

  公开（公告）日：1991-06-26
• US4882347A
  申请人：——

  公开号：US4882347A

  公开（公告）日：1989-11-21
• [EN] COMBINED USE OF N-IMIDAZOLYL DERIVATIVES OF BICYCLIC COMPOUNDS AND CYCLOSPORINE IN THERAPY
  申请人：FARMITALIA CARLO ERBA S.R.L.

  公开号：WO1991000102A1

  公开（公告）日：1991-01-10

  (EN) The invention relates to the use of N-imidazolyl derivatives of bicyclic compounds of general formula (I), wherein (a) compound $g(a) is (II) wherein Y completes a single bond or is oxygen or a -CH2- group and the symbol --- represents a single or double bond or (b) compound $g(a) is (III) and the symbol --- represents a double bond; one of R1, R2, R3 and R4 is -CH2OH, C2-C4 acyl, (IV), -COOR7, -CH2COOR7, (V), (VI) or (VII) in which each of R7, R8 and R9 is independently hydrogen or C1-C4 alkyl, and the others are independently chosen from hydrogen, hydroxy, halogen, C1-C4 alkyl, C1-C4 alkoxy and -COOR7 wherein R7 is as defined above; and one of R5 and R6 is hydrogen and the other is hydrogen, C1-C6 alkyl or phenyl; or a pharmaceutically acceptable salt thereof, in particular in combination with cyclosporin A. The compounds obtained are useful in preventing and/or treating cyclosporin A-induced nephrosis in mammals.(FR) L'invention concerne l'emploi de dérivés de N-imidazolyle de composés bicycliques de la formule générale (I), dans laquelle (a) le composé $g(a) représente (II) dans laquelle Y complète une seule liaison ou représente oxygène ou un groupe -CH2-, et le symbole --- représente une liaison simple ou double, ou (b) le composé $g(a) représente (III) et le symbole --- représente une double liaison; un des éléments suivants R1, R2, R3 et R4 représente -CH2OH, acyle contenant 2 à 4 atomes de carbone, (IV), -COOR7, -CH2COOR7, (V), (VI) ou (VII) dans lesquelles R7, R8 et R9 représentent chacun indépendamment hydrogène ou alkyle contenant 1 à 4 atomes de carbone, et les autres sont choisis indépendamment entre hydrogène, hydroxy, halogène, alkyle contenant 1 à 4 atomes de carbone, alcoxy contenant 1 à 4 atomes de carbone et -COOR7 dans lequel R7 est défini comme ci-dessus; l'un des éléments R5 et R6 représente hydrogène et l'autre représente hydrogène, C1-C6 alkyle ou phényle; ou un sel pharmaceutiquement acceptable de ceux-ci, notamment en combinaison avec la cyclosporine A. Les composés obtenus sont utiles pour prévenir et/ou pour traiter la néphrose induite par la cyclosporine A chez les mammifères.
• N-imidazolyl derivatives of the napththalene and chroman rings as thromboxane A2 synthase inhibitors
  作者：P Cozzi、U Branzoli、G Carganico、C Ferti、A Pillan、D Severino、R Tonani

  DOI：10.1016/0223-5234(91)90103-t

  日期：1991.6

  A series of N-imidazol-1-yl derivatives of 1,2-dihydronaphthalene, 1,2,3,4-tetrahydronaphthalene, 2H-1-benzopyran and some related compounds were synthesized and tested as inhibitors of thromboxane A2 synthase in ex vivo experiments with orally treated rats. Some compounds showed good activity which was confirmed in experiments in vitro in rabbit whole blood. Some structural requirements for significant TxA2 synthase inhibitory activity are discussed. The selected 5,6-Dihydro-7-(H-1-imidazol-1-yl)-2-naphthalene-carboxylic acid (compound 7) was conformationally analysed using the Sybyl molecular model system in comparison with dazoxiben. Compound 7 was further pharmacologically investigated and on the basis of its interesting activities in vitro, ex vivo and in vivo and its low toxicity was selected for clinical investigation.