methyl 2-methylbenzo[b]thiophene-3-carboxylate | 762288-24-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: methyl 2-methylbenzo[b]thiophene-3-carboxylate
• 英文别名: 2-methyl-benzo[b]thiophene-3-carboxylic acid methyl ester；Methyl 2-methylbenzothiophene-3-carboxylate；methyl 2-methyl-1-benzothiophene-3-carboxylate
• CAS: 762288-24-4
• 化学式: C₁₁H₁₀O₂S
• 分子量: 206.265
• InChiKey: LEMPHIYYILSVLY-UHFFFAOYSA-N

物化性质

• 沸点：
  313.0±22.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-methylbenzo[b]thiophene-3-carboxylate 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 反应 4.0h， 生成 Methyl 2-(bromomethyl)-1-benzothiophene-3-carboxylate
  参考文献：
  名称：

  EP3192794

  摘要：

  公开号：
• 作为产物：
  描述：

  2-甲基苯并噻吩 在 三氯化铝 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 生成 methyl 2-methylbenzo[b]thiophene-3-carboxylate
  参考文献：
  名称：

  5-HT2C antagonists based on fused heterotricyclic templates: Design, synthesis and biological evaluation

  摘要：

  Design, synthesis and properties of a new tricyclic series of selective 5-HT2C receptor antagonists are reported. Conformational analysis of a 2-phenyl-dihydropyrrolone scaffold suggested that ring fusion, locking coplanarity between the rings of this moiety, might be tolerated by the 5-HT2C receptor. An interesting effect of this is the change of the nature of the carbon-carbon double bond of the lactam ring from vinylic to aromatic. The changes were found to result in a favourable profile at both, receptor and in vivo level. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.034

文献信息

• [EN] COMPOUNDS HAVING ACTIVITY AT 5HT2C RECEPTOR AND USES THEREOF<br/>[FR] COMPOSES AYANT UNE ACTIVITE AU NIVEAU DU RECEPTEUR 5HT2C ET LEURS UTILISATIONS
  申请人：GLAXO GROUP LTD

  公开号：WO2004081010A1

  公开（公告）日：2004-09-23

  Compounds of formula (I) and pharmaceutically acceptable salts thereof are disclosed: wherein Q is phenyl or a 6-membered heteroaromatic group containing at least one nitrogen atom; A is -(CH2-CH2)-, -(CH=CH)-, -(CH2)3-, -C(CH3)2-, -(CH=CH-CH2)-, or a group -(CHR3)- wherein R3 is hydrogen, halogen, hydroxy, cyano, nitro, C1-6alkyl, C3-7cycloalkyl, C3-7cycloalkyloxy, haloC1-6alkyl, C1-6alkoxy, haloC1-6alkoxy or C1-6alkylthio; B is O, S or NR11, wherein R11 is hydrogen, C1-6alkyl optionally substituted by C1-6alkoxy, or is C1-6alkanoyl optionally substituted by C1-6alkoxy; R1 is halogen, cyano, C1-6alkyl, C3-7cycloalkyl, C3-7cycloalkyloxy, C1-6alkoxy, C1-6alkylthio, hydroxy, amino, mono- or di-C1- 6alkylamino, an N-linked 4 to 7 membered heterocyclic group, nitro, haloC1-6alkyl, haloC1-6alkoxy, aryl, arylC1-6alkyl, arylC1-6alkyloxy, arylC1-6alkylthio, COR4 (wherein R4 is amino, mono- or di-C1-6alkylamino or an N-linked 4 to 7 membered heterocyclic group), COOR5 or COR6 (wherein R5 and R6 are independently hydrogen or C1-6alkyl); p is 0, 1 or 2 or 3; R2 is hydrogen, halogen, hydroxy, cyano, nitro, C1-6alkyl, C1-6alkanoyl, C3-7cycloalkyl, C3-7cycloalkyloxy, haloC1-6alkyl, C1-6alkoxy, haloC1-6alkoxy, C1-6alkylthio, amino, mono- or di-C1-6alkylamino or an N-linked 4 to 7 membered heterocyclic group; X is oxygen, sulfur, -CH2- or NR8 wherein R8 is hydrogen or C1-6alkyl; Y is a single bond, -CH2-, -(CH2)2- or -CH=CH-; and Z is an optionally substituted N-linked heterocyclic group or a C-linked 4 to 7 membered heterocyclic group containing at least one nitrogen, or Z is -NR9R10 where R9 and R10 are independently hydrogen or C1-6alkyl. Method of preparation and uses thereof in therapy, such as for example in treatment of depression and anxiety, are also disclosed.

  公开了具有式（I）的化合物及其药学上可接受的盐：其中Q是苯或含有至少一个氮原子的6元杂芳基团；A是-(CH2-CH2)-，-(CH=CH)-，-(CH2)3-，-C(CH3)2-，-(CH=CH-CH2)-，或一个-(CHR3)-基团，其中R3是氢，卤素，羟基，氰基，硝基，C1-6烷基，C3-7环烷基，C3-7环烷氧基，卤代C1-6烷基，C1-6烷氧基，卤代C1-6烷氧基或C1-6烷基硫基；B是O，S或NR11，其中R11是氢，C1-6烷基，可选择地被C1-6烷氧基取代，或是C1-6烷酰基，可选择地被C1-6烷氧基取代；R1是卤素，氰基，C1-6烷基，C3-7环烷基，C3-7环烷氧基，C1-6烷氧基，C1-6烷基硫基，羟基，氨基，单或双C1-6烷基氨基，N-连接的4到7成员杂环基团，硝基，卤代C1-6烷基，卤代C1-6烷氧基，芳基，芳基C1-6烷基，芳基C1-6烷氧基，芳基C1-6烷硫基，COR4（其中R4是氨基，单或双C1-6烷基氨基或N-连接的4到7成员杂环基团），COOR5或COR6（其中R5和R6独立地是氢或C1-6烷基）；p是0，1，2或3；R2是氢，卤素，羟基，氰基，硝基，C1-6烷基，C1-6烷酰基，C3-7环烷基，C3-7环烷氧基，卤代C1-6烷基，C1-6烷氧基，卤代C1-6烷氧基，C1-6烷基硫基，氨基，单或双C1-6烷基氨基或N-连接的4到7成员杂环基团；X是氧，硫，-CH2-或NR8，其中R8是氢或C1-6烷基；Y是单键，-CH2-，-(CH2)2-或-CH=CH-；Z是一个可选择地取代的N-连接杂环基团或含有至少一个氮的C-连接的4到7成员杂环基团，或Z是-NR9R10，其中R9和R10独立地是氢或C1-6烷基。还公开了其制备方法及在治疗中的用途，例如在抑郁症和焦虑症的治疗中。
• Compounds having activity at 5ht2c receptor and uses thereof
  申请人：Hamprecht Dieter

  公开号：US20060281786A1

  公开（公告）日：2006-12-14

  Compounds of formula (I) and pharmaceutically acceptable salts thereof are disclosed: wherein Q is phenyl or a 6-membered heteroaromatic group containing at least one nitrogen atom; A is —(CH 2 —CH 2 )—, —(CH═CH)—, —(CH 2 ) 3 —, —C(CH 3 ) 2 —, —(CH═CH—CH 2 )—, or a group —(CHR 3 )— wherein R 3 is hydrogen, halogen, hydroxy, cyano, nitro, C 16 alkyl, C 3-7 cycloalkyl, C 3-7 cycloalkyloxy, haloC 1-6 alkyl, C 1-6 alkoxy, haloC 1-6 alkoxy or C 1-6 alkylthio; B is O, S or NR 11 , wherein R 11 is hydrogen, C 1-6 alkyl optionally substituted by C 1-6 alkoxy, or is C 1-6 alkanoyl optionally substituted by C 1-6 alkoxy; R 1 is halogen, cyano, C 1-6 alkyl, C 3-7 cycloalkyl, C 3-7 cycloalkyloxy, C 1-6 alkoxy, C 1 - 6 alkylthio, hydroxy, amino, mono- or di-C 1-6 alkylamino, an N-linked 4 to 7 membered heterocyclic group, nitro, haloC 1 6 alkyl, haloC 1-6 alkoxy, aryl, arylC 1-6 alkyl, arylC 1-6 alkyloxy, arylC 1-6 alkylthio, COR 4 (wherein R 4 is amino, mono- or di-C 1-6 alkylamino or an N-linked 4 to 7 membered heterocyclic group), COOR 5 or COR 6 (wherein R 5 and R 6 are independently hydrogen or C 1-6 alkyl); p is 0, 1 or 2 or 3; R 2 is hydrogen, halogen, hydroxy, cyano, nitro, C 1-6 alkyl, C 1-6 alkanoyl, C 3-7 cycloalkyl, C 3-7 cycloalkyloxy, haloC 1-6 alkyl, C 1-6 alkoxy, haloC 1-6 alkoxy, C 1-6 alkylthio, amino, mono- or di-C 1-6 alkylamino or an N-linked 4 to 7 membered heterocyclic group; X is oxygen, sulfur, —CH 2 — or NR 8 wherein R 8 is hydrogen or C 1-6 alkyl; Y is a single bond, —CH 2 —, —(CH 2 ) 2 13 or —CH═CH—; and Z is an optionally substituted N-linked heterocyclic group or a C-linked 4 to 7 membered heterocyclic group containing at least one nitrogen, or Z is —NR 9 R 10 where R 9 and R 10 are independently hydrogen or C 1-6 alkyl. Method of preparation and uses thereof in therapy, such as for example in treatment of depression and anxiety, are also disclosed.

  公开了化合物式（I）及其药学上可接受的盐：其中Q是苯基或含有至少一个氮原子的6元杂环芳基基团；A是—（CH2—CH2）—，—（CH═CH）—，—（CH2）3—，—C（CH3）2—，—（CH═CH—CH2）—或—（CHR3）—基团，其中R3是氢，卤素，羟基，氰基，硝基，C16烷基，C3-7环烷基，C3-7环烷氧基，卤代C1-6烷基，C1-6烷氧基，卤代C1-6烷氧基或C1-6烷基硫基；B是O，S或NR11，其中R11是氢，C1-6烷基（可选地被C1-6烷氧基取代），或者是C1-6烷酰基（可选地被C1-6烷氧基取代）；R1是卤素，氰基，C1-6烷基，C3-7环烷基，C3-7环烷氧基，C1-6烷氧基，C1-6烷基硫基，羟基，氨基，单或双C1-6烷基氨基，N-连接的4至7元杂环基团，硝基，卤代C1-6烷基，卤代C1-6烷氧基，芳基，芳基C1-6烷基，芳基C1-6烷氧基，芳基C1-6烷基硫基，COR4（其中R4是氨基，单或双C1-6烷基氨基或N-连接的4至7元杂环基团），COOR5或COR6（其中R5和R6分别是氢或C1-6烷基）；p是0，1，2或3；R2是氢，卤素，羟基，氰基，硝基，C1-6烷基，C1-6烷酰基，C3-7环烷基，C3-7环烷氧基，卤代C1-6烷基，C1-6烷氧基，卤代C1-6烷氧基，C1-6烷基硫基，氨基，单或双C1-6烷基氨基或N-连接的4至7元杂环基团；X是氧，硫，—CH2—或NR8，其中R8是氢或C1-6烷基；Y是单键，—CH2—，—（CH2）2—或—CH═CH—；Z是可选取代的N-连接杂环基团或含有至少一个氮原子的C-连接4至7元杂环基团，或Z是—NR9R10，其中R9和R10分别是氢或C1-6烷基。公开了制备方法及其在治疗中的用途，例如治疗抑郁症和焦虑症。
• Tricyclic Compounds Useful as Inhibitors of Kinases
  申请人：Truchon Jean-Francois

  公开号：US20100048551A1

  公开（公告）日：2010-02-25

  The present invention provides inhibitors of kinases, specifically IκB kinases, JAK1, JAK2, JAK3 and TYK2. The invention also provides for compositions comprising such inhibitory compounds and methods of inhibiting said kinase activity by administering the compound to a patient in need of treatment for myeloproliferative disorders, cancer or NF-κB-mediated diseases.

  本发明提供了激酶抑制剂，特别是IκB激酶、JAK1、JAK2、JAK3和TYK2的抑制剂。本发明还提供了包含这种抑制性化合物的组合物，并通过将该化合物用于需要治疗骨髓增生性疾病、癌症或NF-κB介导疾病的患者来抑制该激酶活性的方法。
• Metal‐Free Arylation of Benzothiophenes at C4 by Activation as their Benzothiophene S‐Oxides
  作者：Ranjana Bisht、Mihai V Popescu、Zhen He、Ameer M Ibrahim、Giacomo E M Crisenza、Robert S Paton、David John Procter

  DOI：10.1002/anie.202302418

  日期：——

  key structures in materials and medicines and methods for their selective C−H functionalization are highly prized. Activation of benzothiophenes bearing electron-withdrawing groups at C3 as their S-oxides enables formal C−H/C−H coupling with phenols to access C4 arylated benzothiophenes. Computational studies suggest the intermediacy of a π-complex between the benzothiophene and a phenoxonium cation

  苯并噻吩是材料和药物中的关键结构，其选择性 C−H 官能化方法受到高度重视。 C3 处带有吸电子基团的苯并噻吩作为其S氧化物被激活，使得 C−H/C−H 与苯酚发生正式偶联，得到 C4 芳基化苯并噻吩。计算研究表明，苯并噻吩和苯氧鎓阳离子之间存在 π 配合物的中介作用。
• SUSTAINED HIV PROTEASE INHIBITOR
  申请人：Shionogi & Co., Ltd.

  公开号：EP3192794A1

  公开（公告）日：2017-07-19

  The present invention provides useful compounds for HIV protease inhibitor. A compound represented by formula or its pharmaceutically acceptable salt Formula: wherein ring A is R4 is -Y-Z, hydrogen atom, halogen, hydroxy and the like, R5 is hydrogen atom, halogen, hydroxy and the like, R6 is each independently halogen, hydroxy, carboxy and the like, ring A may be substituted with said R6 at any substitutable position(s), a is an integer of 0 to 7, ring B is substituted or unsubstituted aromatic carbocyclyl, or substituted or unsubstituted aromatic heterocyclyl, ring C is substituted or unsubstituted aromatic carbocyclyl, substituted or unsubstituted non-aromatic carbocyclyl, substituted or unsubstituted aromatic heterocyclyl, or substituted or unsubstituted non-aromatic heterocyclyl, R1 is -Y-Z, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl and the like, R2 and R3 are each independently -Y-Z or hydrogen atom, provided that at least one of R1, R2, R3 and R4 is a group represented by formula: -Y-Z, Y is a bond, or a spacer of any combination selected from the group consisting of -O-, -S-, -NR7-, -C(=O)-, -SO-, -SO2-, -NR7-C(=O)-, -C(=O)-NR7-, -NR7-C(=O)-NR7-, -NR7-C(=O)-O-, -SO2-NR7-, -NR7-SO2-, substituted or unsubstituted alkylene, substituted or unsubstituted alkenylene, substituted or unsubstituted alkynylene, substituted or unsubstituted aromatic carbocyclediyl, substituted or unsubstituted non-aromatic carbocyclediyl, substituted or unsubstituted aromatic heterocyclediyl and substituted or unsubstituted non-aromatic heterocyclediyl, R7 are each independently hydrogen atom, hydroxy, carboxy and the like, and Z is substituted aromatic carbocyclyl, substituted non-aromatic carbocyclyl, substituted aromatic heterocyclyl or substituted non-aromatic heterocyclyl.

  本发明提供了用于 HIV 蛋白酶抑制剂的有用化合物。由式或其药学上可接受的盐代表的化合物 式： 其中环 A 是 R4为-Y-Z、氢原子、卤素、羟基等、 R5 是氢原子、卤素、羟基等、 R6 各自独立地为卤素、羟基、羧基等、 环 A 可在任何可取代的位置被所述 R6 取代、 a 是 0 至 7 的整数、 环 B 是取代或未取代的芳香族碳环，或取代或未取代的芳香族杂环、 环 C 是取代或未取代的芳香族碳环，取代或未取代的非芳香族碳环，取代或未取代的芳香族杂环，或取代或未取代的非芳香族杂环、 R1 是-Y-Z、取代或未取代的烷基、取代或未取代的烯基、取代或未取代的炔基等、 R2 和 R3 各自独立地为-Y-Z 或氢原子、 条件是 R1、R2、R3 和 R4 中至少有一个是由式表示的基团：-Y-Z、 Y 是键，或选自以下组别的任意组合的间隔物：-O-、-S-、-NR7-、-C(=O)-、-SO-、-SO2-、-NR7-C(=O)-、-C(=O)-NR7-、-NR7-C(=O)-NR7-、-NR7-C(=O)-O-、-SO2-、-NR7-SO2-、取代或未取代的亚烷基、取代或未取代的烯基、取代或未取代的炔基、取代或未取代的芳香族碳环基、取代或未取代的非芳香族碳环基、取代或未取代的芳香族杂环基和取代或未取代的非芳香族杂环基、 R7 各自独立地为氢原子、羟基、羧基等，以及 Z 是取代的芳香族碳环基、取代的非芳香族碳环基、取代的芳香族杂环基或取代的非芳香族杂环基。