methyl 2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate | 478239-03-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡咯类
• 英文名称: methyl 2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate
• CAS: 478239-03-1
• 化学式: C₉H₉NO₂S
• mdl: MFCD08277222
• 分子量: 195.242
• InChiKey: AGEYHRRXKZBQTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  70.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以91%的产率得到2-methyl-4H-thieno[3,2-b]pyrrole-5-carbohydrazide
  参考文献：
  名称：

  Discovery of thienopyrrolotriazine derivatives to protect mitochondrial function against Aβ-induced neurotoxicity

  摘要：

  Recovery of mitochondrial dysfunction has gained increasing attention as an alternative therapeutic strategy for Alzheimer's disease (AD). Recent studies suggested that the 18 kDa mitochondrial translocator protein (TSPO) has the potential to serve as a drug target for the treatment of AD. In this study, we generated a structure-based pharmacophore model and virtually screened a commercial library, identifying SVH07 as a virtual hit, which contained a tricyclic core structure, thieno[2',3':4,5]pyrrolo[1,2-d] [1,2,4]triazine group. A series of SVH07 analogues were synthesized and their effects on the mitochondrial membrane potential and ATP production were determined by using neuronal cells under A beta-induced toxicity. Among these analogues, compound 26 significantly recovered mitochondrial membrane depolarization and ATP production. In vitro binding assays indicated that SVH07 and 26 showed high affinities to TSPO with the IC50 values in a nanomolar range. We believe that compound 26 is a promising lead compound for the development of TSPO-targeted mitochondrial functional modulators with therapeutic potential in AD. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.09.033
• 作为产物：
  描述：

  5-甲基-2-噻吩甲醛 在 sodium methylate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 5.5h， 生成 methyl 2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate
  参考文献：
  名称：

  摘要：

  The influence of catalysts, acid chlorides, and solvents on the acylation of methyl 2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate was studied. The use of AlCl3 allows the regioselective introduction of the acyl group into position 3 to be performed, whereas the acyl group is regioselectively introduced into position 6 of thienopyrrole when SnCl4 is used.

  DOI：

  10.1023/a:1023435605723

文献信息

• Synthesis and Structure of 4-Indolyl-5-(thieno[3,2-b]pyrrol-6-yl)imidazoles
  作者：M. M. Krayushkin、I. P. Sedishev、V. N. Yarovenko、I. V. Zavarzin、L. G. Vorontsova、Z. A. Starikova、B. V. Nabatov

  DOI：10.1007/s11178-005-0345-1

  日期：2005.9

  A procedure was proposed for regioselective acylation of methyl 2-methyl-4H-thieno[3,2-b]-pyrrole-5-carboxylate with 2-(3-indolyl)-2-oxoacetyl chloride. Reactions of the resulting methyl 6-[2-(3-indolyl)-1,2-dioxoethyl]-2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate with aromatic aldehydes and ammonium acetate in acetic acid afforded the corresponding methyl 6-[2-aryl-4-(3-indolyl)imidazol-5-yl]-2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylates. The structure of methyl 6-[2-(4-chlorophenyl)-4-(3-indolyl)imidazol-5-yl]-2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate was studied by X-ray analysis.

  提出了一种用于选择性乙酰化甲基2-甲基-4H-噻吩[3,2-b]吡咯-5-羧酸酯与2-(3-吲哚基)-2-氧代乙酰氯的程序。将所得甲基6-[2-(3-吲哚基)-1,2-二氧代乙基]-2-甲基-4H-噻吩[3,2-b]吡咯-5-羧酸酯与芳香醛和乙酸铵在乙酸中反应，得到了相应的甲基6-[2-芳基-4-(3-吲哚基)咪唑-5-基]-2-甲基-4H-噻吩[3,2-b]吡咯-5-羧酸酯。通过X射线分析研究了甲基6-[2-(4-氯苯基)-4-(3-吲哚基)咪唑-5-基]-2-甲基-4H-噻吩[3,2-b]吡咯-5-羧酸酯的结构。
• ——
  作者：M. M. Krayushkin、V. N. Yarovenko、S. L. Semenov、V. Z. Shirinyan、A. Yu. Martynkin、B. M. Uzhinov

  DOI：10.1023/a:1021660014609

  日期：——

  The reaction of 3,4-dichlorocyclobutene-1,2-dione with methyl 2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate occurs at the thiophene ring of the latter, yielding a product in which the thienopyrrole fragments are linked through a dioxocyclobutene ring. Oxidation of this product with hydrogen peroxide gives previously unknown thermally stable photochromic system containing thienopyrrole groups linked through a 2,5-dioxofuran bridge.
• Synthesis of Photochromic 1,2-Dihetarylethene Using Regioselective Acylation of Thienopyrroles
  作者：Michael M. Krayushkin、Vladimir N. Yarovenko、Stanislav L. Semenov、Igor V. Zavarzin、Anatoliy V. Ignatenko、Andrey Yu. Martynkin、Boris M. Uzhinov

  DOI：10.1021/ol026705i

  日期：2002.10.1

  [GRAPHICS]The influence of catalysts, acid chlorides, and solvents in the acylation of methyl 2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate was studied. Conditions for the regioselective acylation processes were found. Thienopyrrole-based photochrome was synthesized for the first time.
• WO2023/151697
  申请人：——

  公开号：——

  公开（公告）日：——
• Discovery of thienopyrrolotriazine derivatives to protect mitochondrial function against Aβ-induced neurotoxicity
  作者：TaeHun Kim、Woo Seung Son、Mohammad Neaz Morshed、Ashwini M. Londhe、Seo Yun Jung、Jong-Hyun Park、Woo-Kyu Park、Sang Min Lim、Ki Duk Park、Sung Jin Cho、Kyu-Sung Jeong、Jiyoun Lee、Ae Nim Pae

  DOI：10.1016/j.ejmech.2017.09.033

  日期：2017.12

  Recovery of mitochondrial dysfunction has gained increasing attention as an alternative therapeutic strategy for Alzheimer's disease (AD). Recent studies suggested that the 18 kDa mitochondrial translocator protein (TSPO) has the potential to serve as a drug target for the treatment of AD. In this study, we generated a structure-based pharmacophore model and virtually screened a commercial library, identifying SVH07 as a virtual hit, which contained a tricyclic core structure, thieno[2',3':4,5]pyrrolo[1,2-d] [1,2,4]triazine group. A series of SVH07 analogues were synthesized and their effects on the mitochondrial membrane potential and ATP production were determined by using neuronal cells under A beta-induced toxicity. Among these analogues, compound 26 significantly recovered mitochondrial membrane depolarization and ATP production. In vitro binding assays indicated that SVH07 and 26 showed high affinities to TSPO with the IC50 values in a nanomolar range. We believe that compound 26 is a promising lead compound for the development of TSPO-targeted mitochondrial functional modulators with therapeutic potential in AD. (C) 2017 Elsevier Masson SAS. All rights reserved.