1-(4,5-二甲基-2-噻吩)乙酮 | 66587-69-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(4,5-二甲基-2-噻吩)乙酮
• 英文名称: (4,5-dimethyl-2-thienyl)(methyl)methanone
• 英文别名: 1-(4,5-dimethyl-[2]thienyl)-ethanone；1-(4,5-Dimethyl-[2]thienyl)-aethanon；2-acetyl-4,5-dimethylthiophene；4,5-Dimethyl-2-acetothienon；5-Acetyl-2,3-dimethylthiophene；1-(4,5-dimethylthiophen-2-yl)ethanone
• CAS: 66587-69-7
• 化学式: C₈H₁₀OS
• 分子量: 154.233
• InChiKey: OANYJDXGTCXYAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4,5-二甲基-2-噻吩)乙酮 在 五氯化磷 、 盐酸羟胺 、 四氯化锡 、 barium carbonate 作用下， 以 乙醚 、 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 19.25h， 生成 N-[3-(3-chlorobenzoyl)-4,5-dimethylthiophen-2-yl]acetamide
  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：

  3-甲基噻吩醛 在 四氯化锡 、 一水合肼 、 乙二醇 作用下， 以 苯 为溶剂， 反应 2.25h， 生成 1-(4,5-二甲基-2-噻吩)乙酮
  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

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。
• 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。
• [EN] PYRAZOLOTHIAZOLE CARBOXAMIDES AND THEIR USES AS PDGFR INHIBITORS<br/>[FR] PYRAZOLOTHIAZOLE CARBOXAMIDES ET LEURS UTILISATIONS EN TANT QU'INHIBITEURS DE PDGFR
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：WO2022136509A1

  公开（公告）日：2022-06-30

  The disclosure is directed to compounds of formula (I),and pharmaceutically acceptable salts thereof. Pharmaceutical compositions comprising compounds of formula (I), as well as methods of their use and preparation, are also described.

  本公开涉及式(I)的化合物及其药学上可接受的盐。还描述了包含式(I)化合物的制药组合物，以及它们的使用和制备方法。
• 2-ACYLAMINOTHIAZOLE DERIVATIVE OR SALT THEREOF
  申请人：Astellas Pharma Inc.

  公开号：EP3153511A1

  公开（公告）日：2017-04-12

  To provide a compound useful as an active ingredient of a pharmacological composition for the treatment of urinary storage symptoms, dysuria, lower urinary tract diseases, and the like. [Solution] The inventors perfected the present invention after discovering that thiazole derivatives substituted at position 2 by pyrazinylcarbonylamino are exceptional muscarinic M3 receptor positive allosteric modulators and can be expected to serve as agents for the prevention or treatment of urinary bladder and urinary tract diseases involving bladder contraction mediated by muscarinic M3 receptors. The 2-acylaminothiazole derivatives or salts thereof of the present invention can be expected to serve as agents for the prevention or treatment of urinary bladder and urinary tract diseases involving bladder contraction mediated by muscarinic M3 receptors, e.g., underactive bladder and the like.

  提供一种化合物，作为治疗储尿症状、排尿困难、下尿路疾病等的药理组合物的有效成分。[解决方案]本发明者发现在第 2 位被吡嗪基羰基氨基取代的噻唑衍生物是一种特殊的毒蕈碱 M3 受体正异位调节剂，可望作为预防或治疗涉及毒蕈碱 M3 受体介导的膀胱收缩的膀胱和尿路疾病的药物，从而完善了本发明。本发明的2-乙酰氨基噻唑衍生物或其盐可望用作预防或治疗涉及毒蕈碱M3受体介导的膀胱收缩的膀胱和尿路疾病的药物，例如膀胱功能不全等。
• The Willgerodt Reaction in the Heterocyclic Series. II. Some Compounds of the α- and β-Thienyl Series
  作者：Joseph A. Blanchette、Ellis V. Brown

  DOI：10.1021/ja01150a103

  日期：1951.6