ethyl 5,6-dimethoxy-3-(3-thienyl)-1H-indole-2-carboxylate | 1380695-72-6

• 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: ethyl 5,6-dimethoxy-3-(3-thienyl)-1H-indole-2-carboxylate
• 英文别名: ethyl 5,6-dimethoxy-3-thiophen-3-yl-1H-indole-2-carboxylate
• CAS: 1380695-72-6
• 化学式: C₁₇H₁₇NO₄S
• 分子量: 331.392
• InChiKey: WGEYOYVWYVYRCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  88.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 5,6-dimethoxy-3-(3-thienyl)-1H-indole-2-carboxylate 在 水 、 lithium hydroxide 作用下， 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and Agonistic Activity at the GPR35 of 5,6-Dihydroxyindole-2-carboxylic Acid Analogues

  摘要：

  5,6-Dihydroxyindole-2-carboxylic acid (DHICA), an intermediate of melanin synthesis and an eumelanin building block, was recently discovered to be a GPR35 agonist with moderate potency. Here, we report the synthesis and pharmacological characterization of a series of DHICA analogues against GPR35 using both label-free, dynamic mass redistribution and Tango beta-arrestin translocation assays. This led to identification of novel GPR35 agonists with improved potency and/or having biased agonism.

  DOI：

  10.1021/ml300076u
• 作为产物：
  描述：

  6-溴藜芦醛 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 sodium carbonate 、 caesium carbonate 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 生成 ethyl 5,6-dimethoxy-3-(3-thienyl)-1H-indole-2-carboxylate
  参考文献：
  名称：

  Synthesis and Agonistic Activity at the GPR35 of 5,6-Dihydroxyindole-2-carboxylic Acid Analogues

  摘要：

  5,6-Dihydroxyindole-2-carboxylic acid (DHICA), an intermediate of melanin synthesis and an eumelanin building block, was recently discovered to be a GPR35 agonist with moderate potency. Here, we report the synthesis and pharmacological characterization of a series of DHICA analogues against GPR35 using both label-free, dynamic mass redistribution and Tango beta-arrestin translocation assays. This led to identification of novel GPR35 agonists with improved potency and/or having biased agonism.

  DOI：

  10.1021/ml300076u

文献信息

• Expedient synthesis of eumelanin-inspired 5,6-dihydroxyindole-2-carboxylate ethyl ester derivatives
  作者：Andrew H. Aebly、Jeffrey N. Levy、Benjamin J. Steger、Jonathan C. Quirke、Jason M. Belitsky

  DOI：10.1039/c8ra06148c

  日期：——

  Dihydroxyindoles such as 5,6-dihydroxyindole-2-carboxylic acid (DHICA) are the main monomer units of eumelanin, the black to brown pigment in humans, and have emerging biological roles beyond melanin. Elaboration of commercially available 5,6-dimethoxy-2-carboxylate ethyl ester provides ready access to DHICA-inspired small molecules, including 3-(hetero)aryl-indoles and 4,7-di-(hetero)aryl-indoles.

  二羟基吲哚如 5,6-二羟基吲哚-2-羧酸 (DHICA) 是真黑色素的主要单体单元，真黑色素是人体中的黑色至棕色色素，并具有超越黑色素的新兴生物学作用。市售的 5,6-二甲氧基-2-羧酸乙酯的研制提供了对 DHICA 启发的小分子的便捷访问，包括 3-(杂)芳基-吲哚和 4,7-二-(杂)芳基-吲哚。
• [EN] HETEROARYL COMPOUNDS AS AGROCHEMICAL FUNGICIDES<br/>[FR] COMPOSÉS HÉTÉROARYLE EN TANT QUE FONGICIDES AGROCHIMIQUES
  申请人：BASF SE

  公开号：WO2018210660A1

  公开（公告）日：2018-11-22

  The present invention relates to heteroaryl compounds of formula (I) or a compound in the form of a stereoisomer, an agriculturally acceptable salt, a tautomer, an isotopic form, a N-oxide, a S-oxide, a prodrug or mixture thereof. The present invention further relates to the use of a compound of formula (I). Furthermore, the present invention relates to methods for combating phytopathogenic harmful fungi, which methods comprising the steps of treatment of the phytopathogenic fungi, the plant or the plant propagation material selected from seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants, including seedlings and young plants to be protected against fungal attack, stored materials or harvest, or alternately the locus or soil or soil substituents or surfaces therefrom, with at least one compound of formula (I).
• [EN] HETEROARYL COMPOUNDS AS AGROCHEMICAL FUNGICIDES<br/>[FR] COMPOSÉS HÉTÉROARYLES EN TANT QUE FONGICIDES AGROCHIMIQUES
  申请人：BASF SE

  公开号：WO2018210658A1

  公开（公告）日：2018-11-22

  The present invention relates to heteroaryl compounds of formula (I) or a compound in the form of a stereoisomer, an agriculturally acceptable salt, a tautomer, an isotopic form, a N-oxide, a S-oxide, a prodrug or mixture thereof. The present invention further relates to the use of a compound of formula (I). Furthermore, the present invention relates to methods for combating phytopathogenic harmful fungi, which methods comprising the steps of treatment of the phytopathogenic fungi, the plant or the plant propagation material selected from seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants, including seedlings and young plants to be protected against fungal attack, stored materials or harvest, or alternately the locus or soil or soil substituents or surfaces therefrom, with at least one compound of formula (I).
• [EN] HETEROARYL COMPOUNDS AS AGROCHEMICAL FUNGICIDES<br/>[FR] COMPOSÉS HÉTÉROARYLE FAISANT OFFICE DE FONGICIDES AGROCHIMIQUES
  申请人：BASF SE

  公开号：WO2018210661A1

  公开（公告）日：2018-11-22

  The present invention relates to heteroaryl compounds of formula (I) or a compound in the form of a stereoisomer, an agriculturally acceptable salt, a tautomer, an isotopic form, a N-oxide, a S- oxide, a prodrug or mixture thereof. The present invention further relates to the use of a com- pound of formula (I). Furthermore, the present invention relates to methods for combating phy- topathogenic harmful fungi, which methods comprising the steps of treatment of the phytopatho- genic fungi, the plant or the plant propagation material selected from seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants, including seedlings and young plants to be protected against fungal attack, stored materials or harvest, or alternately the locus orsoil or soil substituents or surfaces therefrom, with at least one compound of formula (I).