5-methoxy-3-(1-methylethoxy)-1H-indole-2-carboxylic acid methyl ester | 113525-15-8

• 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
• 英文名称: 5-methoxy-3-(1-methylethoxy)-1H-indole-2-carboxylic acid methyl ester
• 英文别名: methyl 5-methoxy-3-(1-methylethoxy)-1H-indole-2-carboxylate；methyl 5-methoxy-3-propan-2-yloxy-1H-indole-2-carboxylate
• CAS: 113525-15-8
• 化学式: C₁₄H₁₇NO₄
• 分子量: 263.293
• InChiKey: NXBUTNLOOXLFAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  60.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-methoxy-3-(1-methylethoxy)-1H-indole-2-carboxylic acid methyl ester 在 氢氧化钾 、 copper diacetate 、 potassium carbonate 、 copper(I) bromide 作用下， 以 甲醇 、 水 为溶剂， 反应 5.0h， 生成 5-methoxy-3-(1-methylethoxy)-1-phenyl-1H-indole-2-carboxylic acid
  参考文献：
  名称：

  Unangst, Paul C.; Connor, David T.; Stabler, S. Russell, Journal of Heterocyclic Chemistry, 1987, vol. 24, p. 811 - 815

  摘要：

  DOI：
• 作为产物：
  描述：

  2-((羧甲基)氨基)-5-甲氧基苯甲酸 在 硫酸 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 56.0h， 生成 5-methoxy-3-(1-methylethoxy)-1H-indole-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Unangst, Paul C.; Connor, David T.; Stabler, S. Russell, Journal of Heterocyclic Chemistry, 1987, vol. 24, p. 811 - 815

  摘要：

  DOI：

文献信息

• Inhibition of E-Selectin-, ICAM-1-, and VCAM-1-Mediated Cell Adhesion by Benzo[b]thiophene-, Benzofuran-, Indole-, and Naphthalene-2-carboxamides: Identification of PD 144795 as an Antiinflammatory Agent
  作者：Diane H. Boschelli、James B. Kramer、Sonya S. Khatana、Roderick J. Sorenson、David T. Connor、Mark A. Ferin、Clifford D. Wright、Mark E. Lesch、Kathleen Imre

  DOI：10.1021/jm00022a026

  日期：1995.10

  reported that 3-alkoxybenzo[b]thiophene-2-carboxamides exemplified by 1, 5-methoxy-3-(1-methylethoxy)benzo[b]thiophene-2-carboxamide, decreased the adherence of neutrophils to activated endothelial cells by inhibiting the upregulation of the adhesion molecules E-selectin and ICAM-1 on the surface of the endothelium. This finding is extended here to a series of 3-thiobenzo[b]thiophene-2-carboxamides and also

  以前有报道说，以1，5-甲氧基-3-（1-甲基乙氧基）苯并[b]噻吩-2-羧酰胺为例的3-烷氧基苯并[b]噻吩-2-甲酰胺降低了中性粒细胞对活化内皮细胞的粘附通过抑制内皮细胞表面粘附分子E-选择素和ICAM-1的上调。该发现在这里扩展到一系列的3-硫代苯并[b]噻吩-2-羧酰胺以及1的杂环类似物，包括苯并呋喃，吲哚和萘。抑制E-选择蛋白和ICAM-1表达的化合物对VCAM-1的表达具有相同的作用。PD 144795，亚砜类似物1，即5-甲氧基-3-（1-甲基乙氧基）苯并[b]噻吩-2-羧酰胺1-氧化物（44）在几种炎症模型中具有口服活性。
• Indole-2-carboxamides as inhibitors of cell adhesion
  申请人：Warner-Lambert Company

  公开号：US05424329A1

  公开（公告）日：1995-06-13

  3-Substituted-indole-2-carboxamides are described as agents which inhibit leukocyte adherence to vascular endothelium and, as such, are effective therapeutic agents for treating inflammatory diseases. Certain of these compounds are novel and methods of manufacture are also described. Certain of the indole-2-carboxamides also inhibit the activation of human immunodeficiency virus (HIV), latent in infected humans.

  3-取代吲哚-2-羧酰胺被描述为抑制白细胞粘附到血管内皮的药物，并且作为有效的治疗药物用于治疗炎症性疾病。其中一些化合物是新颖的，并且还描述了其制造方法。其中一些吲哚-2-羧酰胺也能抑制潜伏在感染人体内的人类免疫缺陷病毒（HIV）的激活。
• Inhibition of adhesion molecule expression by N-alkylthiopyridine-benzo[b]thiophene-2-carboxamides
  作者：Diane H. Boschelli、David T. Connor、Mark E. Lesch、Denis J. Schrier

  DOI：10.1016/0968-0896(96)00046-6

  日期：1996.4

  The surface levels of ICAM-1 and E-selectin on activated endothelial cells can be reduced by 3-alkoxybenzo[b]thiophene-2-carboxamides. This property is shared by several N-alkylthiopyridine substituted imides. Combining structural elements of these two diverse series lead to a new class of small molecule inhibitors of adhesion molecule expression.

  3-烷氧基苯并[b]噻吩-2-羧酰胺可降低活化的内皮细胞上ICAM-1和E-选择素的表面水平。该性质由几个N-烷基硫代吡啶取代的酰亚胺共享。这两个不同系列的结构元素的组合导致了一类新的粘附分子表达的小分子抑制剂。
• Novel indolecarboxamidotetrazoles as potential antiallergy agents
  作者：Paul C. Unangst、David T. Connor、S. Russell Stabler、Robert J. Weikert、Mary E. Carethers、John A. Kennedy、David O. Thueson、James C. Chestnut、Richard L. Adolphson、M. C. Conroy

  DOI：10.1021/jm00126a036

  日期：1989.6

  The synthesis and antiallergic potential of a series of novel indolecarboxamidotetrazoles are described. A number of compounds inhibit the release of histamine from anti-IgE-stimulated basophilic leukocytes obtained from allergic donors. Optimal inhibition is exhibited by compounds with 3-alkoxy, 5-methoxy, and 1-phenyl substituents on the indole core structure. Compound 8d (5-methoxy-3-(1-methylethoxy)-1-phenyl-N-1H-tetrazol-5-yl-1H -indole-2-carboxamide; designated CI-949) is a potent inhibitor of histamine release from human basophils and from guinea pig and human chopped lung.
• UNANGST, PAUL C.;CONNOR, DAVID T.;STABLER, S. RUSSELL;WEIKERT, ROBERT J., J. HETEROCYCL. CHEM., 24,(1987) N 3, 811-815
  作者：UNANGST, PAUL C.、CONNOR, DAVID T.、STABLER, S. RUSSELL、WEIKERT, ROBERT J.

  DOI：——

  日期：——