3-(2,2-dimethyl-1,2,3,4-tetrahydronaphthalen-1-yl)-3H-imidazole-4-carboxylic acid methyl ester | 110323-21-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 3-(2,2-dimethyl-1,2,3,4-tetrahydronaphthalen-1-yl)-3H-imidazole-4-carboxylic acid methyl ester
• 英文别名: 1-(2,2-dimethyl-1,2,3,4-tetrahydronaphthalen-1-yl)-5-imidazolecarboxylic acid methyl ester；methyl 1-(1,2,3,4-tetrahydro-2,2-dimethyl-1-naphthalenyl)-1H-imidazole-5-carboxylate；1-(2,2-dimethyltetralin-1-yl)-5-imidazolecarboxylic acid methyl ester；methyl 3-(2,2-dimethyl-3,4-dihydro-1H-naphthalen-1-yl)imidazole-4-carboxylate
• CAS: 110323-21-2
• 化学式: C₁₇H₂₀N₂O₂
• 分子量: 284.358
• InChiKey: LWBZUDPQMGTLDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2,2-dimethyl-1,2,3,4-tetrahydronaphthalen-1-yl)-3H-imidazole-4-carboxylic acid methyl ester 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 水 为溶剂， 生成 3-(2,2-dimethyl-4-oxo-1,2,3,4-tetrahydronaphthalen-1-yl)-3H-imidazole-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Herbicidal imidazole derivatives

  摘要：

  公式I中的1,5-取代咪唑衍生物 ##STR1## 其立体化学异构体及其盐具有有用的除草活性。 取代基R.sup.1、R.sup.2、R.sup.3、R.sup.4、X.sup.1、X.sup.2、X.sup.3、A、L和m的含义如本文所定义。

  公开号：

  US04898607A1
• 作为产物：
  描述：

  2,2-二甲基-3,4-二氢萘-1-酮 在 sodium tetrahydroborate 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 1.33h， 生成 3-(2,2-dimethyl-1,2,3,4-tetrahydronaphthalen-1-yl)-3H-imidazole-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Structure–Activity Relationships, Pharmacokinetics, and in Vivo Activity of CYP11B2 and CYP11B1 Inhibitors

  摘要：

  CYP11B2, the aldosterone synthase, and CYP11B1, the cortisol synthase, are two highly homologous enzymes implicated in a range of cardiovascular and metabolic diseases. We have previously reported the discovery of LCI699, a dual CYP11B2 and CYP11B1 inhibitor that has provided clinical validation for the lowering of plasma aldosterone as a viable approach to modulate blood pressure in humans, as well normalization of urinary cortisol in Cushing's disease patients. We now report novel series of aldosterone synthase inhibitors with single-digit nanomolar cellular potency and excellent physicochemical properties. Structure-activity relationships and optimization of their oral bioavailability are presented. An illustration of the impact of the age of preclinical models on pharmacokinetic properties is also highlighted. Similar biochemical potency was generally observed against CYP11B2 and CYP11B1, although emerging structure-selectivity relationships were noted leading to more CYP11B1-selective analogs.

  DOI：

  10.1021/acs.jmedchem.5b00407

文献信息

• Herbicidal 1,5-substituted 1H-imidazoles
  申请人：Janssen Pharmaceutica N.V.

  公开号：US04878940A1

  公开（公告）日：1989-11-07

  Novel herbicidal 1,5-substituted 1H-imidazole derivatives, compositions containing these compounds as active ingredients, and a method for controlling weeds, preferably selectively in crops of useful plants. Further the invention also relates to a process for making these novel compounds.

  新型除草剂1,5-取代的1H-咪唑衍生物，含有这些化合物作为活性成分的组合物，以及一种用于控制杂草的方法，最好是在有用植物作物中选择性地控制。此外，该发明还涉及制备这些新型化合物的方法。
• 1H-imidazole-5-carboxylic acid derivatives
  申请人：JANSSEN PHARMACEUTICA N.V.

  公开号：EP0277384A3

  公开（公告）日：1990-05-23

  A method of controlling weeds by applying thereto or to the locus thereof of an imidazole derivative of formula wherein R1 is hydrogen or mercapto;L is cyano or a radical of formulaX is 1-indanyl, 1-tetrahydronaphthalenyl, 5-benzocycloheptanyl, 4-tetrahydrobenzothienyl, 4-tetrahydroben- zofuryl, 5-tetrahydroquinolyl, 5-tetrahydroisoquinolyl, 8-tetrahydroquinolyl, 8-tetrahydroisoquinolyl, 9,10-dihydro-9-antracenyl, 9H-fluoren-9-yl, 5-dibenzo[a,d]-cycloheptenyl, 5-dibenzo[a,d]cycloheptanyl or 1-dihydronaphthalenyl each unsubstituted or substituted; or X is a group or a group - ; whereinn is 0, 1 or 2 or two; A is hydrogen, optionally substituted C3-C7cycloalkyl or pyridinyl, pyrimidinyl, naphthalenyl, f6ranyt and thienyl, each unsubstituted or substituted; Z is naphthalenyl, thienyl, furanyl, pyrimidinyl, phenyl or pyridinyl, each unsubstituted or substituted;a salt or stereoisomeric form thereof, novel compounds for use in said method; herbicidal compositions containing such compounds as active ingredient and methods of preparing said compounds.

  一种通过将咪唑衍生物应用于杂草或其生长地点来控制杂草的方法，其中该衍生物的结构式为R1为氢或巯基；L为氰基或结构式的基团；X为1-吲哚基、1-四氢萘基、5-苯并环庚基、4-四氢苯并噻吩基、4-四氢苯并噻喃基、5-四氢喹啉基、5-四氢异喹啉基、8-四氢喹啉基、8-四氢异喹啉基、9,10-二氢-9-蒽基、9H-芴-9-基、5-二苯并[a,d]-环庚基、5-二苯并[a,d]环庚基或1-二氢萘基，每个未取代或取代；或X为一个基团或一个基团-；其中n为0、1或2或两个；A为氢，可选地取代的C3-C7环烷基或吡啶基、嘧啶基、萘基、富兰基和噻吩基，每个未取代或取代；Z为萘基、噻吩基、呋喃基、嘧啶基、苯基或吡啶基，每个未取代或取代；其盐或立体异构体形式，用于该方法的新化合物；含有这种化合物作为活性成分的除草剂组合物以及制备这种化合物的方法。
• Method for controlling weeds
  申请人：Janssen Pharmaceutica N.V.

  公开号：US05246915A1

  公开（公告）日：1993-09-21

  A method for controlling weeds preferably in the crops of useful plants by using a 5-imidazolecarboxylic acid derivative; herbicidal compositions containing the same; novel 5-imidazolecarboxylic acid derivatives.

  一种用5-咪唑羧酸衍生物控制杂草的方法，优选在有用植物作物中使用；含有该衍生物的除草剂组合物；新颖的5-咪唑羧酸衍生物。
• Imidazole derivatives
  申请人：Ciba-Geigy Corporation

  公开号：US05000777A1

  公开（公告）日：1991-03-19

  1,5-substituted imidazole derivatives of formula I ##STR1## the stereochemically isomeric forms thereof, and the salts thereof, have useful herbicidal properties. The substituents R.sup.1, R.sup.2, R.sup.3, R.sup.4, X.sup.1, X.sup.2, X.sup.3, A, L and m have the meanings defined herein.

  公式I中的1,5-取代咪唑衍生物 ##STR1## 其立体化学异构体和其盐具有有用的除草特性。 取代基R.sup.1，R.sup.2，R.sup.3，R.sup.4，X.sup.1，X.sup.2，X.sup.3，A，L和m的含义在此定义。
• ORGANIC COMPOUNDS
  申请人：Adams Christopher

  公开号：US20100048562A1

  公开（公告）日：2010-02-25

  The present invention provides a compound of formula I: said compound is inhibitor of aldosterone synthase (CYP11B2), and/or 11 beta-hydroxylase (CYP11B1), and/or aromatase, and thus can be employed for the treatment of a disorder or disease mediated by aldosterone synthase, aromatase, or CYP11B1. Accordingly, the compound of formula I can be used in treatment of hypokalemia, hypertension, congestive heart failure, renal failure, in particular, chronic renal failure, restenosis, atherosclerosis, syndrome X, obesity, nephropathy, post-myocardial infarction, coronary heart diseases, increased formation of collagen, fibrosis and remodeling following hypertension and endothelial dysfunction. Finally, the present invention also provides a pharmaceutical composition.

  本发明提供了一种公式I的化合物：该化合物是醛固酮合成酶（CYP11B2）和/或11β-羟化酶（CYP11B1）和/或芳香化酶的抑制剂，因此可用于治疗由醛固酮合成酶、芳香化酶或CYP11B1介导的疾病或疾病。因此，公式I的化合物可用于治疗低钾血症、高血压、充血性心力衰竭、肾衰竭，特别是慢性肾衰竭、再狭窄、动脉粥样硬化、X综合征、肥胖症、肾病、心肌梗死后、冠心病、胶原形成增加、高血压和内皮功能障碍后的纤维化和重塑。最后，本发明还提供了一种制药组合物。