N-(4,5-dimethyl-thiophen-2-yl)acetamide | 51948-20-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(4,5-dimethyl-thiophen-2-yl)acetamide
• 英文别名: 4,5-dimethyl-2-acetamidothiophen；N-(4,5-dimethyl-thiophen-2-yl)-acetamide；2-acetamido-4,5-dimethylthiophene；N-(4,5-dimethylthiophen-2-yl)acetamide
• CAS: 51948-20-0
• 化学式: C₈H₁₁NOS
• mdl: MFCD00185815
• 分子量: 169.247
• InChiKey: CPTWNJFKDSOTAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.375
• 拓扑面积：
  57.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4,5-dimethyl-thiophen-2-yl)acetamide 在 氢氧化钾 、 四氯化锡 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 11.25h， 生成 (2-Amino-4,5-dimethylthiophen-3-yl)(m-tolyl)methanone
  参考文献：
  名称：

  2-Amino-3-aroyl-4,5-alkylthiophenes:  Agonist Allosteric Enhancers at Human A₁ Adenosine Receptors

  摘要：

  2-Amino-3-benzoylthiophenes are allosteric enhancers (AE) of agonist activity at the A(1) adenosine receptor. The present report describes syntheses and assays of the AE activity at the human A(1)AR (hA(1)AR) of a panel of compounds consisting of nine 2-amino-3-aroylthiophenes (3a-i), eight 2-amino-3-benzoyl-4,5-dimethylthiophenes (12a-h), three 3-aroyl-2-carboxy-4,5-dimethylthiophenes (15a-c), 10 2-amino-3-benzoyl-5,6-dihydro-4H-cyclopenta[b]thiophenes (17a-j), 14 2-amino-3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophenes (18a-n), and 15 2-amino-3-benzoyl-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophenes (19a-o). An in vitro assay employing the A(1)AR agonist [I-125]ABA and membranes from CHO-K1 cells stably expressing the hA(1)AR measured, as an index of AE activity, the ability of a candidate AE to stabilize the agonist-A(1)AR-G protein ternary complex. Compounds 3a-i had little or no AE activity, and compounds 12a-h had only modest activity, evidence that AE activity depended absolutely on the presence of at least a methyl group at C-4 and C-5. Compounds 17a-c lacked AE activity, suggesting the 2-amino group is essential. Polymethylene bridges linked thiophene C-4 and C-5 of compounds 17a-j, 18a-n, and 19a-o. AE activity increased with the size of the -(CH2)(n)- bridge, n = 3 < n = 4 < n = 5. The 3-carbethoxy substituents of 17a, 18a, and 19a did not support AE activity, but a 3-aroyl group did. Bulky (or hydrophobic) substituents at the meta and para positions of the 3-benzoyl group and also 3-naphthoyl groups greatly enhanced activity. Thus, the hA(1)AR contains an allosteric binding site able to accommodate 3-aroyl substituents that are bulky and/or hydrophobic but not necessarily planar. A second region in the allosteric binding site interacts constructively with alkyl substituents at thiophene C-4 and/or C-5.

  DOI：

  10.1021/jm010081p
• 作为产物：
  描述：

  2-乙酰氨基-4,5-二甲基噻吩-3-羧酸 生成 N-(4,5-dimethyl-thiophen-2-yl)acetamide
  参考文献：
  名称：

  Functional derivatives of thiophene

  摘要：

  DOI：

  10.1007/bf00477559

文献信息

• 2-amino-3-aroyl-4,5 alkylthiophenes: agonist allosteric enhancers at human A1 adenosine receptors
  申请人：——

  公开号：US20030078248A1

  公开（公告）日：2003-04-24

  The present invention relates to a compound of formula (I): 1 wherein: R 3 is selected from the group consisting of 1-napthyl, 2-napthyl and cycloalkylphenyl; and R 4 and R 5 taken together form a ring having from 5 to 10 carbon atoms. Additionally, the invention provides a therapeutic method for preventing or treating a pathological condition or symptom in a mammal subject, such as a human, wherein increased angiogenesis is desired, comprising administering to a mammal in need of such therapy an effective amount of the aforementioned thiophene selective adenosine A 1 allosteric enhancer.

  本发明涉及以下式（I）的化合物：其中：R3选择自1-萘基、2-萘基和环烷基苯基所组成的群；以及R4和R5一起形成含有5到10个碳原子的环。此外，本发明提供了一种治疗方法，用于预防或治疗哺乳动物主体（如人类）中的病理状况或症状，其中需要增加血管生成，包括向需要此类治疗的哺乳动物中施用上述噻吩选择性腺苷A1受体变构增强剂的有效量。
• A versatile new synthesis of quinolines and related fused pyridines. Part 7. The conversion of acetamidothiophens into thienopyridines
  作者：Otto Meth-Cohn、Brahma Narine、Brian Tarnowski

  DOI：10.1039/p19810001531

  日期：——

  good yield with equimolar amounts of dimethylformamide and phosphoryl chloride in hot dichloroethane. However, undersimilar conditions but with three mol of phosphoryl chloride, 6-chlorothieno[2,3-b]pyridines are obtained. Use of phosphoryl chloride as solvent (7 mol) with three mol of dimethylformamide gives good yields of 6-chlorothieno-[2,3-b]pyridine-5-carbaldehydes. Similarly, thieno[3,2-b]-and thieno[3

  将5-取代的2-对乙酰氨基噻吩与等摩尔量的二甲基甲酰胺和磷酰氯在热的二氯乙烷中以良好的产率转化为2-对乙酰氨基噻吩-3-甲醛。然而，在相似的条件下，但是具有三摩尔的磷酰氯，获得了6-氯噻吩并[2,3- b ]吡啶。与三摩尔二甲基甲酰胺一起使用磷酰氯作为溶剂（7摩尔），可以得到6-氯噻吩并-[2,3 - b ]吡啶-5-甲醛的良好收率。类似地，thieno [3,2- b ]-和thieno [3,4- b]-吡啶分别得自3-乙酰氨基噻吩和2，5-二甲基-3-乙酰氨基噻吩。探索了这些反应的机理，并将其与从乙酰苯胺形成相关喹啉中涉及的那些机理进行了比较，并表明它们涉及初始的环甲酰化。显示2-氯喹啉的类似形成具有有限的潜力。
• 2-Amino-3-aroyl-4,5 alkylthiophenes: agonist allosteric enhancers at human A1 adenosine receptors
  申请人：——

  公开号：US20040180948A1

  公开（公告）日：2004-09-16

  The present invention relates to a compound of formula (I): 1 wherein: R 3 is selected from the group consisting of 1-napthyl, 2-napthyl and cycloalkylphenyl; and R 4 and R 5 taken together form a ring having from 5 to 10 carbon atoms. Additionally, the invention provides a therapeutic method for preventing or treating a pathological condition or symptom in a mammal subject, such as a human, wherein increased angiogenesis is desired, comprising administering to a mammal in need of such therapy an effective amount of the aforementioned thiophene selective adenosine A 1 allosteric enhancer.

  本发明涉及一种式（I）的化合物：1其中：R3选自1-萘基，2-萘基和环烷基苯基的群组；以及R4和R5一起形成一个具有5至10个碳原子的环。此外，本发明提供了一种治疗方法，用于预防或治疗哺乳动物受体中的病理状况或症状，例如人类，其中需要增加血管生成，包括向需要此种治疗的哺乳动物中注射上述噻吩选择性腺苷A1异构增强剂的有效剂量。
• PYRAZOLYL DERIVATIVES
  申请人：University of Dundee

  公开号：EP2980076A1

  公开（公告）日：2016-02-03

  The present invention relates to N-heterocyclic sulphonamide compounds, in particular pyrazole sulphonamide compounds, and their use as N-myristoyl transferase inhibitors.

  本发明涉及 N-杂环磺酰胺化合物，特别是吡唑磺酰胺化合物，以及它们作为 N-肉豆蔻酰转移酶抑制剂的用途。
• The Preparation and Formylation of 2-Acetamidothiophenes
  作者：Otto Meth-Cohn、Bramha Narine

  DOI：10.1055/s-1980-28947

  日期：——