methyl 4-[5-(5,7-dimethylnaphthalen-2-yl)-1H-pyrrol-2-yl]benzoate | 196519-83-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: methyl 4-[5-(5,7-dimethylnaphthalen-2-yl)-1H-pyrrol-2-yl]benzoate
• CAS: 196519-83-2
• 化学式: C₂₄H₂₁NO₂
• 分子量: 355.436
• InChiKey: XGLTXQUWONESLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 4-[5-(5,7-dimethylnaphthalen-2-yl)-1H-pyrrol-2-yl]benzoate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 4-[5-(5,7-dimethylnaphthalen-2-yl)-1H-pyrrol-2-yl]benzoic acid
  参考文献：
  名称：

  Syntheses and evaluation of naphthalenyl- and chromenyl-pyrrolyl-benzoic acids as potent and selective retinoic acid receptor α agonists

  摘要：

  Synthesis and structure-activity relationships (SAR) of RAR alpha-selective agonists are discussed. 4-[5-(5,8-Dimethyl-2H-3-chromenyl)-1H-2-pyrrolyl]benzoic acid (12a), which possesses a flat structural moiety and an oxygen atom at the hydrophobic part, showed highly selective transactivation activity at the RAR alpha receptor. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00067-6
• 作为产物：
  描述：

  2-Acryloyl-5,7-dimethylnaphthalene 在 ammonium acetate 、 sodium acetate 、 3-苄基羟乙基甲基噻唑氯化锂 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 methyl 4-[5-(5,7-dimethylnaphthalen-2-yl)-1H-pyrrol-2-yl]benzoate
  参考文献：
  名称：

  Syntheses and evaluation of naphthalenyl- and chromenyl-pyrrolyl-benzoic acids as potent and selective retinoic acid receptor α agonists

  摘要：

  Synthesis and structure-activity relationships (SAR) of RAR alpha-selective agonists are discussed. 4-[5-(5,8-Dimethyl-2H-3-chromenyl)-1H-2-pyrrolyl]benzoic acid (12a), which possesses a flat structural moiety and an oxygen atom at the hydrophobic part, showed highly selective transactivation activity at the RAR alpha receptor. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00067-6

文献信息

• FUSED-RING CARBOXYLIC ACID DERIVATIVES
  申请人：Eisai Co., Ltd.

  公开号：EP0889032A1

  公开（公告）日：1999-01-07

  Fused-ring carboxylic acid derivatives represented by general formula (A) and pharmacologically acceptable salts thereof, which can provide medicines excellent in retinoic acid receptor agonist activities, wherein the symbolrepresents a single or double bond; and each of X, Y, Z, P, Q, U, V and W represents -O-, -S- or a group represented by formula (a), wherein Rk (k:1-8) represents hydrogen, halogeno, optionally substituted lower alkyl, etc., and either R7 or R8 represents a group represented by formula (b), wherein rings A and B represent each independently an optionally substituted aromatic hydrocarbon or unsaturated heterocyclic ring; and D represents an optionally protected carboxyl group.

  通式(A)代表的融合环羧酸衍生物及其药理学上可接受的盐，可提供维甲酸受体激动剂活性极佳的药物，其中符号代表单键或双键；X、Y、Z、P、Q、U、V 和 W 各自代表-O-、-S- 或式(a)代表的基团，其中 Rk (k:1-8) 代表氢、卤素、任选取代的低级烷基等、以及 R7 或 R8 代表由式（b）表示的基团，其中环 A 和 B 各自独立地代表任选取代的芳香烃或不饱和杂环；以及 D 代表任选保护的羧基。
• RETINOIC ACID AGONISTS AS PREVENTIVE AND THERAPEUTIC AGENTS FOR NEPHRITIS
  申请人：Eisai Co., Ltd.

  公开号：EP1025857A1

  公开（公告）日：2000-08-09

  Therapeutic or preventive agents for system lupus erythematosus, glomerulonephritis, lupus nephritis, idiopathic thrombocytopenic purpura or autoimmune anemia, which can be substituted for conventional steroid preparations or immunosuppressive agents. The active ingredients of the therapeutic or preventive agents are agonists for retinoic acid receptors, particularly retinoic receptor, subtype α (i.e., RAR α), and examples of the agonists include (1) carboxylic acid derivatives bearing fused rings as represented by general formula (I) wherein rings L and M are fused with each other, and are each independently an optionally substituted aromatic hydrocarbon ring or an optimally substituted heterocycle; rings A and B are each independently an optionally substituted aromatic hydrocarbon ring or a heterocycle; and D is optionally protected carboxyl, and (2) 4-[(3,5-bistrimethylsilylphenyl)carbonyl]amino}benzoic acid and 42-[5-(3-methoxymethyl-5,6,7,8-tetrahydro-5,5,8,8,-tetramethylnaphthalen-2-yl)-pyrrolyl]}benzoic acid.

  治疗或预防系统性红斑狼疮、肾小球肾炎、狼疮性肾炎、特发性血小板减少性紫癜或自身免疫性贫血的药物，可替代传统的类固醇制剂或免疫抑制剂。治疗剂或预防剂的有效成分是视黄酸受体激动剂，特别是视黄酸受体α亚型（即 RAR α、RAR β 和 RAR β 例子）、RAR α）的激动剂，激动剂的例子包括 (1) 如通式（I）所示的带有融合环的羧酸衍生物，其中环 L 和 M 相互融合，且各自独立地为任选取代的芳香烃环或最佳取代的杂环；(2) 4-[(3,5-二甲基硅基苯基)羰基]氨基}苯甲酸和 42-[5-(3-甲氧基甲基-5,6,7,8-四氢-5,5,8,8,-四甲基萘-2-基)-吡咯基]}苯甲酸。
• US6121309A
  申请人：——

  公开号：US6121309A

  公开（公告）日：2000-09-19
• US6110959A
  申请人：——

  公开号：US6110959A

  公开（公告）日：2000-08-29
• US6258811B1
  申请人：——

  公开号：US6258811B1

  公开（公告）日：2001-07-10