1-(7-甲氧基-3,4-二氢萘-2-基)咪唑 | 89781-56-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-(7-甲氧基-3,4-二氢萘-2-基)咪唑
• 英文名称: 1,2-dihydro-3-(1-imidazolyl)-6-methoxynaphthalene
• 英文别名: 1H-Imidazole, 1-(3,4-dihydro-7-methoxy-2-naphthalenyl)-；1-(7-methoxy-3,4-dihydronaphthalen-2-yl)imidazole
• CAS: 89781-56-6
• 化学式: C₁₄H₁₄N₂O
• 分子量: 226.278
• InChiKey: CRAMMDHXKKDBIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(7-甲氧基-3,4-二氢萘-2-基)咪唑 在 palladium on activated charcoal 盐酸 、 氢气 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以85%的产率得到1-(7-甲氧基-1,2,3,4-四氢萘-2-基)咪唑
  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
• 作为产物：
  描述：

  2-溴-7-甲氧基-3,4-二氢萘-1(2H)-酮 在 sodium tetrahydroborate 、 硫酸 、 溶剂黄146 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 1-(7-甲氧基-3,4-二氢萘-2-基)咪唑
  参考文献：
  名称：

  作为 P450 芳香族、P450 17 和 P450 TxA2 抑制剂的唑取代四氢萘的合成和评价

  摘要：

  寻找用于治疗雌激素和雄激素依赖性癌症以及预防转移的潜在药物、四氢萘酮、四氢萘和在苯核上带有 OCH3 取代基和咪唑 - 4 - 基、咪唑 - 1- 的二氢萘基或 1,2,4-三唑-1-基取代基在 2-位合成，在环之间有和没有 C1-间隔物（化合物 2-26）。在体外测试了这些化合物对三种靶酶 P450 arom（人胎盘微粒体）、P450 17（大鼠睾丸微粒体）和 P450 TxA2（柠檬酸化人全血）的抑制作用。为了检查选择性，在体外进一步测试了一些化合物对 P450 18（牛肾上腺线粒体）、P450 see（牛肾上腺线粒体）和皮质激素形成（醛固酮、皮质酮；ACTH 刺激的大鼠肾上腺组织）的抑制。体内，

  DOI：

  10.1002/ardp.19963290506

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.

  式(I)的化合物 ##STR1## 其中符号表示单键或双键；Z完成单键或为--CH.sub.2 --基团；R.sub.1、R.sub.2、R.sub.3和R.sub.4中的每一个，可以相同或不同，为(a)氢；羟基；卤素；氰基；C.sub.1-C.sub.6烷基；C.sub.1-C.sub.6烷氧基；C.sub.2-C.sub.4酰基或C.sub.2-C.sub.4酰胺基；--SR'，--N(R') (R")，--CH.sub.2 OR'，--COR或--CH.sub.2 COR，其中R为OR'或--N(R') (R")，而R'和R"中的每一个，可以相同或不同，为氢或C.sub.1-C.sub.6烷基；或(b)R.sub.1、R.sub.2、R.sub.3和R.sub.4中的一个为5-四唑基或从--COCH.sub.2 OR'，--CH.dbd.C(R')-COR和--X-C(R') (R")-COR中选择的基团，其中R、R'和R"如上所定义，而X为--O--，--S--或--NH--，其他的如上所述在(a)下定义；R.sub.5和R.sub.6中的一个为氢，而另一个为氢、C.sub.1-C.sub.6烷基、C.sub.3-C.sub.6环烷基或苯环或吡啶环，其中苯环或吡啶环未取代或被1到3个羟基和C.sub.1-C.sub.4烷氧基中选择的取代基所取代；或其药学上可接受的盐，表现出作为血管扩张剂或血小板聚集抑制剂的药理活性。此外，这些化合物及其药学上可接受的盐在治疗偏头痛、糖尿病微血管病、类风湿性关节炎、高血压、消化性溃疡、骨质疏松症、心绞痛、动脉粥样硬化和脂质代谢异常方面有用。
• N-imidazolyl derivatives of bicyclic compounds
  申请人：Farmitalia Carlo Erba, S.p.A.

  公开号：US04602022A1

  公开（公告）日：1986-07-22

  Compounds of the formula (I) ##STR1## wherein the symbol represents a single or a double bond; 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); R.sub.5 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, or a phenyl or 3-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 salt 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 microangiopathy, rheumatoid arthritis, hypertension, peptic ulcers, osteoporosis, angina pectoris, atherosclerosis and dislipidaemies.

  式(I)的化合物 ##STR1## 其中符号表示单键或双键；R.sub.1，R.sub.2，R.sub.3和R.sub.4中的每一个，可能相同或不同，是(a)氢；羟基；卤素；氰基；C.sub.1-C.sub.6烷基；C.sub.1-C.sub.6烷氧基；C.sub.2-C.sub.4酰基或C.sub.2-C.sub.4酰胺基；--SR'，--N(R')(R")，--CH.sub.2 OR'，--COR或--CH.sub.2 COR，其中R为OR'或--N(R')(R")，而R'和R"中的每一个，相同或不同，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.2 OR'，--CH.dbd.C(R')--COR和--X--C(R')(R")--COR中选择的一种基团，其中，R，R'和R"如上所定义，而X为--O--，--S--或--NH--，其余如上(a)中所定义；R.sub.5是氢，C.sub.1-C.sub.6烷基，C.sub.3-C.sub.6环烷基，或苯环或3-吡啶基，其中苯环或吡啶环是未取代的或被1至3个羟基和C.sub.1-C.sub.4烷氧基中的一个取代；或其药学上可接受的盐表现出作为血管扩张剂或血小板聚集抑制剂的药理活性。此外，这些化合物及其药学上可接受的盐在偏头痛、糖尿病微血管病、类风湿性关节炎、高血压、消化性溃疡、骨质疏松症、心绞痛、动脉粥样硬化和脂质代谢异常的治疗中有用。
• Selective Inhibitors of Human Corticosteroid Synthases
  申请人：Hartmann Rolf W.

  公开号：US20090221591A1

  公开（公告）日：2009-09-03

  The invention relates to compounds for selectively inhibiting human corticosteroid synthases CYP1 1 B1 and CYP1 1 B2, and to the production and use thereof for treating hypercortisolism, diabetes mellitus, hyperaldosteronism, cardiac insufficiency, myocardial fibrosis, depression, age-related cognitive decline and metabolic syndrome.

  本发明涉及用于选择性抑制人类皮质类固醇合成酶CYP11B1和CYP11B2的化合物，以及其生产和用于治疗高皮质醇症，糖尿病，高醛固酮症，心力衰竭，心肌纤维化，抑郁症，年龄相关认知衰退和代谢综合征。
• SELEKTIVE HEMMSTOFFE HUMANER CORTICOIDSYNTHASEN
  申请人：Universität des Saarlandes

  公开号：EP1853261B1

  公开（公告）日：2017-01-11
• US4510149A
  申请人：——

  公开号：US4510149A

  公开（公告）日：1985-04-09