2-(1-imidazolyl)-1,2,3,4-tetrahydro-7-carboxy-1-naphthalenol | 85929-03-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(1-imidazolyl)-1,2,3,4-tetrahydro-7-carboxy-1-naphthalenol
• 英文别名: 5,6,7,8-tetrahydro-7-(1H-imidazol-1-yl)-2-naphthalenecarboxylic acid；1,2,3,4-tetrahydro-2-(1-imidazolyl)-7-carboxy-1-naphthalenol；8-Hydroxy-7-imidazol-1-yl-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid
• CAS: 85929-03-9
• 化学式: C₁₄H₁₄N₂O₃
• 分子量: 258.277
• InChiKey: MTUOBMXOZSBCGV-UHFFFAOYSA-N

物化性质

• 熔点：
  240-242 °C
• 沸点：
  564.6±50.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  75.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(1-imidazolyl)-1,2,3,4-tetrahydro-7-carboxy-1-naphthalenol 在 氢气 作用下， 生成 7-(1H-咪唑-1-基)-5,6-二氢-2-萘甲酸
  参考文献：
  名称：

  Carganico; Cozzi, Il Farmaco, 1991, vol. 46, # SUPPL. 1, p. 209 - 231

  摘要：

  DOI：
• 作为产物：
  描述：

  4-苯丁酸乙酯 在 sodium hypochlorite 、 sodium tetrahydroborate 、 三氯化铝 、 hydroxide 、 溴 、 sodium chloride 作用下， 以 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-(1-imidazolyl)-1,2,3,4-tetrahydro-7-carboxy-1-naphthalenol
  参考文献：
  名称：

  Carganico; Cozzi, Il Farmaco, 1991, vol. 46, # SUPPL. 1, p. 209 - 231

  摘要：

  DOI：

文献信息

• N-Imidazolyl derivatives containing naphthalene or indene nucleus
  申请人：Farmitalia Carlo Erba S.p.A.

  公开号：US04510149A1

  公开（公告）日：1985-04-09

  Compounds of the formula (I) ##STR1## wherein the symbol represents a single or a double bond; Z completes a single bond or is a --CH.sub.2 -- group; each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which may be the same or different is (a) hydrogen; hydroxy; halogen; cyano; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 alkoxy; a C.sub.2 -C.sub.4 acyl or C.sub.2 -C.sub.4 acylamino group; --SR', --N(R') (R"), --CH.sub.2 OR', --COR or --CH.sub.2 COR, wherein R is OR' or --N(R') (R") and each of R' and R", being the same or different, is hydrogen or C.sub.1 -C.sub.6 alkyl; or (b) one of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is 5- tetrazolyl or a group selected from --COCH.sub.2 OR', --CH.dbd.C(R')-COR and --X-C(R') (R")-COR, wherein R, R' and R" are as defined above, and X is --O--, --S--, or --NH--, and the others are as defined above under (a); one of R.sub.5 and R.sub.6 is hydrogen and the other is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, or a phenyl or pyridyl ring, wherein the phenyl or pyridyl ring is unsubstituted or substituted by one to three substituents chosen from hydroxy and C.sub.1 -C.sub.4 alkoxy; or pharmaceutically acceptable salts thereof exhibit pharmaceutical activity as vasodilators or blood platelet aggregation inhibitors. Additionally, these compounds and their pharmaceutically acceptable salts are useful in the treatment of migraine, diabetic microangeopathy, rheumatoid arthritis, hypertension, peptic ulcers, osteoporosis, angina pectoris, atherosclerosis and dislipidaemies.

  化合物的结构式为(I) ##STR1## 其中符号表示单键或双键；Z完成一个单键或是一个--CH.sub.2--基团；每个R.sub.1、R.sub.2、R.sub.3和R.sub.4，可能相同也可能不同，是(a) 氢；羟基；卤素；氰基；C.sub.1 -C.sub.6烷基；C.sub.1 -C.sub.6氧烷基；一个C.sub.2 -C.sub.4酰基或C.sub.2 -C.sub.4酰胺基团；--SR'，--N(R')(R")，--CH.sub.2OR'，--COR或--CH.sub.2COR，其中R为OR'或--N(R')(R")，且R'和R"，可能相同也可能不同，是氢或C.sub.1 -C.sub.6烷基；或(b) R.sub.1、R.sub.2、R.sub.3和R.sub.4中的一个是5-四唑基或从--COCH.sub.2OR'，--CH.dbd.C(R')-COR和--X-C(R')(R")-COR中选择的一个基团，其中R、R'和R"如上所定义，X为--O--，--S--或--NH--，其他的如(a)下定义；R.sub.5和R.sub.6中的一个是氢，另一个是氢、C.sub.1 -C.sub.6烷基、C.sub.3 -C.sub.6环烷基，或苯基或吡啶环，其中苯基或吡啶环未取代或通过一个到三个羟基和C.sub.1 -C.sub.4氧烷基取代；或其药学上可接受的盐作为血管扩张剂或抗血小板聚集抑制剂具有药理活性。此外，这些化合物及其药学上可接受的盐对治疗偏头痛、糖尿病微血管病变、类风湿性关节炎、高血压、消化性溃疡、骨质疏松症、心绞痛、动脉硬化和脂质代谢紊乱有用。
• 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.
• Eur. J. Med. Chem. 1991, 26,423-433
  作者：

  DOI：——

  日期：——
• FONTANA, ERMINIA;VICARIO, GIAN PIERO, J. LABELL. COMPOUNDS AND RADIOPHARM., 29,(1991) N, C. 853-858
  作者：FONTANA, ERMINIA、VICARIO, GIAN PIERO

  DOI：——

  日期：——
• US4492707A
  申请人：——

  公开号：US4492707A

  公开（公告）日：1985-01-08