5-羟基-2-甲基-1H-吲哚-3-羧酸 | 71982-15-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 5-羟基-2-甲基-1H-吲哚-3-羧酸
• 英文名称: 5-hydroxy-2-methyl-1H-indole-3-carboxylic acid
• 英文别名: 5-hydroxy-2-methyl-indole-3-carboxylic acid；5-Hydroxy-2-methyl-indol-3-carbonsaeure；5-hydroxy-2-methylindole-3-carboxylic acid；5-Hydroxy-2-Methylindole-3-Carboxylate
• CAS: 71982-15-5
• 化学式: C₁₀H₉NO₃
• mdl: MFCD01365791
• 分子量: 191.186
• InChiKey: FHSZQYNWIIHBAX-UHFFFAOYSA-N

物化性质

• 沸点：
  491.5±40.0 °C(Predicted)
• 密度：
  1.480±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  73.3
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  5-羟基-2-甲基-1H-吲哚-3-羧酸 、 溴甲苯 在 potassium carbonate 作用下， 以 水 、 乙腈 为溶剂， 以22%的产率得到二苄醚
  参考文献：
  名称：

  Inhibitors of phospholipase enzymes

  摘要：

  这项发明涉及化合物和药物组合物，用于治疗或预防哺乳动物体内的炎症症状，方法包括给予一般式的新型药用化合物或其药用盐，其中R1-R5如规范中定义。

  公开号：

  US06500853B1
• 作为产物：
  描述：

  5-羟基-2-甲基吲哚-3-羧酸乙酯 在 水 、 sodium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 48.0h， 以75%的产率得到5-羟基-2-甲基-1H-吲哚-3-羧酸
  参考文献：
  名称：

  5-Hydroxyindole-2-carboxylic Acid Amides: Novel Histamine-3 Receptor Inverse Agonists for the Treatment of Obesity

  摘要：

  Obesity is a major risk factor in the development of conditions such as hypertension, hyperglycemia, dyslipidemia, coronary artery disease, and cancer. Several pieces of evidence across different species, including primates, underscore the implication of the histamine 3 receptor (H3R) in the regulation of food intake and body weight and the potential therapeutic effect Of H3R inverse agonists. A pharmacophore model, based on public information and validated by previous investigations, was used to design several potential scaffolds. Out of these scaffolds. the 5-hydroxyindole-2-carboxylic acid amide appeared to be of great potential as a novel series of H-3 inverse agonist. Extensive structure-activity relationships revealed the interconnectivity of microsomal clearance and hERG (human ether-a-go-go-related gene) affinity with lipophilicity, artificial membrane permeation, and basicity. This effort led to the identification of compounds reversing the (R)-alpha-methylhistamine-induced water intake increase in Wistar rats and, further, reducing food intake in diet-induced obese Sprague-Dawley rats. Of these, the biochemical, pharmacokinetic, and pharmacodynamic characteristics of (4,4-difluoropiperidin-1-yl)[1-isopropyl-5-(1-isopropylpiperidin-4-yloxy)1H-indol-2-yl]-methanone 36 are detailed.

  DOI：

  10.1021/jm900409x

文献信息

• Functionalized heterocycles as modulators of chemokine receptor function and methods of use therefor
  申请人：Millennium Pharmaceuticals, Inc.

  公开号：US20030064991A1

  公开（公告）日：2003-04-03

  Disclosed are novel compounds having the formula 1 or a physiologically acceptable salt, amide, ester or prodrug thereof. The compounds can be used to modulate (antagonize, agonize) chemokine receptor function. Also disclosed is a method for treating a patient having an inflammatory disease and/or viral infection comprising administering an effective amount of a compound of Formula I. In particular embodiments, the invention is a method for treating a patient infected with HIV.

  揭示了具有以下结构式的新化合物 1 或其生理上可接受的盐、酰胺、酯或前药。这些化合物可用于调节（拮抗、激动）趋化因子受体功能。还揭示了一种治疗患有炎症性疾病和/或病毒感染的患者的方法，包括给予结构式I的化合物的有效量。在特定实施例中，本发明是一种治疗感染HIV的患者的方法。
• INDOLE-3-CARBOXYLIC ACID AMIDE, ESTER, THIOAMIDE AND THIOL ESTER COMPOUNDS BEARING ARYL OR HETEROARYL GROUPS HAVING SPHINGOSINE-1-PHOSPHATE (S1P) RECEPTOR ANTAGONIST BIOLOGICAL ACTIVITY
  申请人：Beard Richard L.

  公开号：US20070191313A1

  公开（公告）日：2007-08-16

  The invention provides compounds represented by the formula I, each of which compounds may have sphingosine-1-phosphate receptor agonist and or antagonist biological activity: and wherein the variables Y, R 4 , n, A, X, Z, R 1 , o, R 3 , R 2 and p are as defined in the specification. These compounds are useful for treating a disease or condition selected from the group consisting of glaucoma, dry eye, angiogenesis, cardiovascular conditions and diseases, and wound healing

  该发明提供了由式I表示的化合物，每种化合物可能具有鞘氨醇-1-磷酸受体激动剂和/或拮抗剂生物活性：其中变量Y、R4、n、A、X、Z、R1、o、R3、R2和p如规范中所定义。这些化合物对于治疗从青光眼、干眼、血管生成、心血管疾病和疾病以及伤口愈合等一组疾病或状况是有用的。
• 3-indolecarboxamides for control of circulatory diseases
  申请人：Yoshitomi Pharmaceutical Industries, Ltd.

  公开号：US04581355A1

  公开（公告）日：1986-04-08

  3-Indolecarboxamide compounds of the formula: ##STR1## inclusive of pharmaceutically acceptable acid addition salt and/or hydrate forms thereof, wherein R.sup.1 is hydrogen or C.sub.1-4 alkyl; each of R.sup.2 and R.sup.3 is hydrogen, halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, benzyloxy, C.sub.2-6 alkanoyloxy or hydroxy; R.sup.4 is hydrogen or C.sub.1-4 alkyl; R.sup.5 is hydrogen, halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or hydroxy; R.sup.6 is hydrogen or C.sub.1-4 alkyl; X is oxygen, sulfur or direct bond; each of k and m is an integer of 1 to 3; and n is 1 or 2, are useful as drug for the prevention and treatment of various circulatory diseases.

  式为：##STR1## 包括其药学上可接受的酸加盐和/或水合物形式，其中R.sup.1是氢或C.sub.1-4烷基；R.sup.2和R.sup.3中的每一个是氢，卤素，C.sub.1-4烷基，C.sub.1-4烷氧基，苄氧基，C.sub.2-6烷酰氧基或羟基；R.sup.4是氢或C.sub.1-4烷基；R.sup.5是氢，卤素，C.sub.1-4烷基，C.sub.1-4烷氧基或羟基；R.sup.6是氢或C.sub.1-4烷基；X是氧，硫或直接键；k和m中的每一个是1至3的整数；n是1或2，可用于预防和治疗各种循环系统疾病的药物。
• Nenitzescu, Buletinul Societatii de Chimie din Romania, vol. 11, p. 37
  作者：Nenitzescu

  DOI：——

  日期：——
• HAKAO, TATSU;SAJTO, TADAMASA;TEHRASAVA, MITIO;TAXARA, TEHTSUDZI
  作者：HAKAO, TATSU、SAJTO, TADAMASA、TEHRASAVA, MITIO、TAXARA, TEHTSUDZI

  DOI：——

  日期：——