3-<4-Methyl-<2>thienyl>-acrylsaeure | 5834-14-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 3-<4-Methyl-<2>thienyl>-acrylsaeure
• 英文别名: 3-(4-methyl-thiophen-2-yl)-acrylic acid；3-(4-Methylthiophen-2-yl)prop-2-enoic acid
• CAS: 5834-14-0
• 化学式: C₈H₈O₂S
• 分子量: 168.216
• InChiKey: CXPDJQZSEXRKDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-<4-Methyl-<2>thienyl>-acrylsaeure 在 氢气 、 palladium(II) hydroxide 作用下， 以 乙醇 为溶剂， 25.0~75.0 ℃ 、103.42 kPa 条件下， 反应 19.0h， 生成 3-Methyl-5,6-dihydro-cyclopentathiophen-4-on
  参考文献：
  名称：

  Tricyclic pyrazoles part 7. Discovery of potent and selective dihydrothienocyclopentapyrazole derived CB2 ligands

  摘要：

  A series of dihydrothienocyclopentapyrazole-based derivatives was synthesized and evaluated for the affinity at CBI and CB2 receptors. The major term, the 6-methyl-1-(1,4-dichloropheny1)-N-piperidiny1)-1,4-dihydrothieno[2',3'-4,5]cyclopenta[1,2-c]pyrazole-3-carboxamide (6a), displayed a high affinity and good selectivity for CB2 receptors (Ki values of 2.30 nM for CB2 receptor and 440 nM for CB1 receptors respectively). Subsequent analogue preparation resulted in the identification of compounds such as 6b, 6d, 6e, 6k, 6l, 6m, 6s and 6t that showed 1.3-485 fold selectivity for CB2 receptors with potencies in the 1.1-7.2 nM range. These compounds profiled as full agonists at CB2 receptor in an inhibition assay of P-ERK 1/2 up regulation in HL-60 cells. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.08.042
• 作为产物：
  描述：

  4-甲基噻吩-2-甲醛 、 丙二酸 在 哌啶 、 吡啶 作用下， 以65%的产率得到3-<4-Methyl-<2>thienyl>-acrylsaeure
  参考文献：
  名称：

  Tricyclic pyrazoles part 7. Discovery of potent and selective dihydrothienocyclopentapyrazole derived CB2 ligands

  摘要：

  A series of dihydrothienocyclopentapyrazole-based derivatives was synthesized and evaluated for the affinity at CBI and CB2 receptors. The major term, the 6-methyl-1-(1,4-dichloropheny1)-N-piperidiny1)-1,4-dihydrothieno[2',3'-4,5]cyclopenta[1,2-c]pyrazole-3-carboxamide (6a), displayed a high affinity and good selectivity for CB2 receptors (Ki values of 2.30 nM for CB2 receptor and 440 nM for CB1 receptors respectively). Subsequent analogue preparation resulted in the identification of compounds such as 6b, 6d, 6e, 6k, 6l, 6m, 6s and 6t that showed 1.3-485 fold selectivity for CB2 receptors with potencies in the 1.1-7.2 nM range. These compounds profiled as full agonists at CB2 receptor in an inhibition assay of P-ERK 1/2 up regulation in HL-60 cells. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.08.042

文献信息

• 4-Amino-thieno[3,2-c]pyridine-7-carboxylic acid amides
  申请人：Luk Kin-Chun

  公开号：US20050256154A1

  公开（公告）日：2005-11-17

  Disclosed are novel 4-amino-thieno[3,2-c]pyridine-7-carboxylic acid amides, and their pharmaceutically acceptable salts and esters, that are selective inhibitors of KDR and/or FGFR kinases. These compounds and their pharmaceutically acceptable salts are anti-proliferative agents useful in the treatment or control of solid tumors, in particular solid cancerous tumors of the breast, colon, lung and prostate. Also disclosed are pharmaceutical compositions containing these compounds and methods of treating cancer using these compounds.

  本发明涉及一种新型的4-氨基噻吩[3,2-c]吡啶-7-羧酸酰胺及其药学上可接受的盐和酯，它们是KDR和/或FGFR激酶的选择性抑制剂。这些化合物及其药学上可接受的盐是抗增殖剂，可用于治疗或控制实体瘤，特别是乳腺癌、结肠癌、肺癌和前列腺癌等实体癌症。还公开了含有这些化合物的制药组合物以及使用这些化合物治疗癌症的方法。
• 4-amino-thieno[3,2-c] pyridine-7-carboxylic acid derivatives
  申请人：Bartkovitz Joseph David

  公开号：US20070060607A1

  公开（公告）日：2007-03-15

  The present invention relates to compounds of the formula medicaments containing them and the use of these compounds as pharmaceutically active agents. The compounds exhibit activity as Raf kinase inhibitors and therefore may be useful for the treatment of diseases mediated by said kinases, especially as anticancer agents.

  本发明涉及公式化合物，包括含有它们的药物以及这些化合物作为药物活性剂的用途。这些化合物表现出Raf激酶抑制剂的活性，因此可能有用于治疗由该激酶介导的疾病，特别是作为抗癌剂。
• 4-AMINO-THIENO[3,2-C]PYRIDINE-7-CARBOXYLIC ACID AMIDES
  申请人：Luk Kin-Chun

  公开号：US20110071147A1

  公开（公告）日：2011-03-24

  Disclosed are novel 4-amino-thieno[3,2-c]pyridine-7-carboxylic acid amides, and their pharmaceutically acceptable salts and esters, that are selective inhibitors of KDR and/or FGFR kinases. These compounds and their pharmaceutically acceptable salts are anti-proliferative agents useful in the treatment or control of solid tumors, in particular solid cancerous tumors of the breast, colon, lung and prostate. Also disclosed are pharmaceutical compositions containing these compounds and methods of treating cancer using these compounds.

  本发明涉及新颖的4-氨基噻吩[3,2-c]吡啶-7-羧酸酰胺及其药学上可接受的盐和酯，它们是选择性抑制KDR和/或FGFR激酶的抑制剂。这些化合物及其药学上可接受的盐是抗增殖剂，可用于治疗或控制实体肿瘤，特别是乳腺、结肠、肺和前列腺的实体癌肿。本发明还涉及含有这些化合物的制药组合物和使用这些化合物治疗癌症的方法。
• Tricyclic pyrazoles part 7. Discovery of potent and selective dihydrothienocyclopentapyrazole derived CB2 ligands
  作者：Giansalvo Pinna、Maria Michela Curzu、Antonio Dore、Paolo Lazzari、Stefania Ruiu、Amedeo Pau、Gabriele Murineddu、Gérard A. Pinna

  DOI：10.1016/j.ejmech.2014.08.042

  日期：2014.10

  A series of dihydrothienocyclopentapyrazole-based derivatives was synthesized and evaluated for the affinity at CBI and CB2 receptors. The major term, the 6-methyl-1-(1,4-dichloropheny1)-N-piperidiny1)-1,4-dihydrothieno[2',3'-4,5]cyclopenta[1,2-c]pyrazole-3-carboxamide (6a), displayed a high affinity and good selectivity for CB2 receptors (Ki values of 2.30 nM for CB2 receptor and 440 nM for CB1 receptors respectively). Subsequent analogue preparation resulted in the identification of compounds such as 6b, 6d, 6e, 6k, 6l, 6m, 6s and 6t that showed 1.3-485 fold selectivity for CB2 receptors with potencies in the 1.1-7.2 nM range. These compounds profiled as full agonists at CB2 receptor in an inhibition assay of P-ERK 1/2 up regulation in HL-60 cells. (C) 2014 Elsevier Masson SAS. All rights reserved.