4-羟基-苯并[b]噻吩-5-羧酸甲酯 | 246177-37-7

• 物质功能分类: 医药中间体 - 杂环化合物 - 噻吩类化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-羟基-苯并[b]噻吩-5-羧酸甲酯
• 英文名称: 4-hydroxybenzo[b]thiophene-5-carboxylic acid methyl ester
• 英文别名: methyl 4-hydroxybenzo[b]thiophene-5-carboxylate；methyl 4-hydroxy-1-benzothiophene-5-carboxylate；methyl 4-hydroxybenzofuran-5-carboxylate；5-methoxycarbonyl-4-hydroxybenzo[b]thiophene
• CAS: 246177-37-7
• 化学式: C₁₀H₈O₃S
• 分子量: 208.238
• InChiKey: RAWQGMFTJYIMMQ-UHFFFAOYSA-N

物化性质

• 熔点：
  98-99 °C
• 沸点：
  332.3±22.0 °C(Predicted)
• 密度：
  1.394±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  74.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-羟基-苯并[b]噻吩-5-羧酸甲酯 在 potassium hydrogencarbonate 、 sodium amide 作用下， 以 乙醚 、 丙酮 为溶剂， 生成 (Z)-3-hydroxy-1-(4-methoxybenzothiophen-5-yl)-3-phenyl-prop-2-en-1-one
  参考文献：
  名称：

  Synthesis of 4-hydroxy-1-methylindole and benzo[b]thiophen-4-ol based unnatural flavonoids as new class of antimicrobial agents☆

  摘要：

  Synthesis of nitrogen and sulfur heterocyclic mimics of furanoflavonoids have been achieved for the first time. Synthesized flavonoid alkaloids and thiophenyl flavonoids have been screened for antifungal and antibacterial activities. All the test compounds barring 25 exhibited antifungal activity. The compound 19 was the best and showed comparable MICs to the known compound karanjin. Compounds 5, 12, 14 and 22 also showed comparable MIC to karanjin. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.12.032
• 作为产物：
  描述：

  methyl 4-oxo-4,5,6,7-tetrahydro-1-benzothiophene-5-carboxylate 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 为溶剂， 以78%的产率得到4-羟基-苯并[b]噻吩-5-羧酸甲酯
  参考文献：
  名称：

  Synthesis of 4-hydroxy-1-methylindole and benzo[b]thiophen-4-ol based unnatural flavonoids as new class of antimicrobial agents☆

  摘要：

  Synthesis of nitrogen and sulfur heterocyclic mimics of furanoflavonoids have been achieved for the first time. Synthesized flavonoid alkaloids and thiophenyl flavonoids have been screened for antifungal and antibacterial activities. All the test compounds barring 25 exhibited antifungal activity. The compound 19 was the best and showed comparable MICs to the known compound karanjin. Compounds 5, 12, 14 and 22 also showed comparable MIC to karanjin. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.12.032

文献信息

• [EN] ARYLAMIDES AND METHODS OF USE THEREOF<br/>[FR] ARYLAMIDES ET LEURS PROCÉDÉS D'UTILISATION
  申请人：GENZYME CORP

  公开号：WO2021113809A1

  公开（公告）日：2021-06-10

  The present disclosure relates to heterocyclic compounds, pharmaceutically acceptable salts thereof, and pharmaceutical preparations thereof. Also described herein are compositions and the use of such compounds in methods of treating diseases and conditions mediated by deficient CFTR activity, in particular cystic fibrosis.

  本公开涉及杂环化合物，其药用盐以及药物制剂。本文还描述了这些化合物的组成以及在治疗由CFTR活性不足介导的疾病和病况的方法中的使用，特别是囊性纤维化。
• Fused thiophone derivatives and drugs containing the same as the active ingredient
  申请人：Ono Pharmaceutical Co., Ltd.

  公开号：US06420391B1

  公开（公告）日：2002-07-16

  The present invention relates to a fused thiophene derivative of the formula (I) (wherein all the symbols are defined as described in the specification) and an inhibitor of producing interleukin-6 and/or interleukin-12 comprising the said derivative as an active ingredient. A fused thiophene derivative of the formula (I) is useful as an agent for the prevention and/or treatment of various inflammatory diseases, sepsis, multiple myeloma, plasma cell leukemia, osteoporosis, cachexia, psoriasis, nephritis, renal cell carcinoma, Kaposi's sarcoma, rheumatoid arthritis, gammopathy, Castleman's disease, atrial myxoma, diabetes mellitus, autoimmune diseases, hepatitis, multiple sclerosis, colitis, graft versus host immune diseases, infectious diseases.

  本发明涉及公式（I）的融合噻吩衍生物（其中所有符号如规范中所述定义），以及包括所述衍生物作为活性成分的抑制产生白细胞介素-6和/或白细胞介素-12的抑制剂。公式（I）的融合噻吩衍生物可用作预防和/或治疗各种炎症性疾病、败血症、多发性骨髓瘤、浆细胞白血病、骨质疏松症、虚弱症、牛皮癣、肾炎、肾细胞癌、卡波西肉瘤、类风湿性关节炎、免疫球蛋白病、卡斯尔曼病、心房黏液瘤、糖尿病、自身免疫疾病、肝炎、多发性硬化、结肠炎、移植物抗宿主免疫疾病、传染病的药剂。
• Heterocycle carboxamides as antiviral agents
  申请人：——

  公开号：US20020025960A1

  公开（公告）日：2002-02-28

  The present invention provides a compound of formula I 1 which is useful as antiviral agents, in particular, as agents against viruses of the herpes family.

  本发明提供了一种化合物，其化学式为I1，可作为抗病毒药物，特别是用作抗疱疹病毒家族的药物。
• A Catalytic Homo-Nazarov Cyclization Protocol for the Synthesis of Heteroaromatic Ring-Fused Cyclohexanones
  作者：Lien H. Phun、Dadasaheb V. Patil、Marchello A. Cavitt、Stefan France

  DOI：10.1021/ol200305n

  日期：2011.4.15

  A general protocol for the catalytic homo-Nazarov cyclization of cyclopropyl heteroaryl ketones has been developed, which employs indium triflate as the promoter. A range of heteroaromatic ring-fused cyclohexanones was synthesized in 56−91% yield using this protocol. An example of a tandem cyclopropanation/homo-Nazarov cyclization is also reported in which the one-pot yield is greater than the overall

  已经开发出用于环丙基杂芳基酮的催化均-纳扎罗夫环化的通用方案，该方案采用三氟甲磺酸铟作为促进剂。使用该方案以56-91％的产率合成了一系列杂芳环稠合的环己酮。还报道了串联环丙烷化/均一-Nazarov环化的一个例子，其中单罐产率大于两个单独步骤的总产率。
• FUSED THIOPHENE DERIVATIVES AND DRUGS CONTAINING THE SAME AS THE ACTIVE INGREDIENT
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：EP1067128A1

  公开（公告）日：2001-01-10

  Fused thiophene derivatives represented by general formula (I) and interleukin-6 and/or interleukin-12 production inhibitors containing these derivatives as the active ingredient (in general formula (I), each symbol has the meaning as defined in the specification). The fused thiophene derivatives represented by general formula (I) are useful as preventives and/or remedies for various inflammatory diseases, sepsis, multiple myeloma, plasma cell leukemia, osteoporosis, cachexia, psoriasis, nephritis, renal cell cancer, Kaposi's sarcoma, chronic rheumatoid arthritis, hypergamma-globulinemia, Curschmann's disease, intraartial myxoma, diabetes, autoimmune diseases, hepatitis, multiple sclerosis, colon inflammation, graft-versus-host disease and infectious diseases.

  通式(I)代表的融合噻吩衍生物和含有这些衍生物作为活性成分的白细胞介素-6和/或白细胞介素-12产生抑制剂（在通式(I)中，每个符号的含义如说明书中所定义）。通式（I）所代表的融合噻吩衍生物可作为各种炎症、败血症、多发性骨髓瘤、浆细胞白血病、骨质疏松症、恶病质、牛皮癣、肾炎、肾细胞癌的预防和/或治疗药物、卡波西肉瘤、慢性类风湿性关节炎、高丙种球蛋白血症、库希曼病、关节内肌瘤、糖尿病、自身免疫性疾病、肝炎、多发性硬化症、结肠炎、移植物抗宿主病和传染病。