2-acetyl-4-methylphenyl thiophene-2-carboxylate | 60072-30-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetyl-4-methylphenyl thiophene-2-carboxylate
• 英文别名: (2-Acetyl-4-methylphenyl) thiophene-2-carboxylate
• CAS: 60072-30-2
• 化学式: C₁₄H₁₂O₃S
• 分子量: 260.313
• InChiKey: SBBMXJZSZKDOQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  71.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-acetyl-4-methylphenyl thiophene-2-carboxylate 在 copper(ll) bromide 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以60%的产率得到[2-(2-bromoacetyl)-4-methylphenyl] thiophene-2-carboxylate
  参考文献：
  名称：

  Rangachari, K.; Mazumdar, A. K. D.; Banerji, K. D., Journal of the Indian Chemical Society, 1980, vol. 57, # 10, p. 1014 - 1016

  摘要：

  DOI：
• 作为产物：
  描述：

  2-噻吩甲酰氯 、 2-羟基-5-甲基苯乙酮 在 吡啶 作用下， 反应 5.0h， 以90%的产率得到2-acetyl-4-methylphenyl thiophene-2-carboxylate
  参考文献：
  名称：

  多功能Chromeno[2,3-c]pyrrol-9(2H)-ones的合成：4-(二甲氨基)吡啶催化Baker-Venkataraman重排反应的研究与应用

  摘要：

  描述了从 1,3-二芳基-1,3-二酮和氨基酸中高效一锅合成多功能 chromeno[2,3-c]pyrrol-9(2H)-ones。该合成基于 4-（二甲氨基）吡啶催化的 Baker-Venkataraman 重排和后续反应。

  DOI：

  10.1002/ejoc.201100435

文献信息

• Synthesis and reactivity of 1-aryl-9H-thieno[3,4-b]chromon-9-ones
  作者：Mikhail M. Krayushkin、Konstantin S. Levchenko、Vladimir N. Yarovenko、Ludmila V. Christoforova、Valery A. Barachevsky、Yury A. Puankov、Tatyana M. Valova、Olga I. Kobeleva、K. Lyssenko

  DOI：10.1039/b9nj00237e

  日期：——

  Methods were developed for the synthesis of 1-aryl-9H-thieno[3,4-b]chromon-9-ones based on the reaction of bromo and dibromo derivatives of 2-methyl-4H-chromon-4-one with thioacetamide in DMF. The thienochromones were modified and their fluorescence properties were studied. Bis(thienochromones) were synthesized by the reaction of thienochromones with ketoaldehydes.

  根据 2-甲基-4H-色-4-酮的溴和二溴衍生物与硫代乙酰胺在 DMF 中的反应，开发了合成 1-芳基-9H-噻吩并[3,4-b]色-9-酮的方法。对这些噻吩一氢色酮进行了修饰，并研究了它们的荧光特性。双（噻吩一氢色酮）是通过噻吩一氢色酮与酮醛反应合成的。
• Discovery of 3-(4-hydroxybenzyl)-1-(thiophen-2-yl)chromeno[2,3-c]pyrrol-9(2H)-one as a phosphodiesterase-5 inhibitor and its complex crystal structure
  作者：Na-Na Shang、Yong-Xian Shao、Ying-Hong Cai、Matthew Guan、Manna Huang、Wenjun Cui、Lin He、Yan-Jun Yu、Lei Huang、Zhe Li、Xian-Zhang Bu、Hengming Ke、Hai-Bin Luo

  DOI：10.1016/j.bcp.2014.02.013

  日期：2014.5

  Phosphodiesterase-5 (PDE5) inhibitors have been approved for the treatment of erectile dysfunction and pulmonary hypertension, but enthusiasm on discovery of PDE5 inhibitors continues for their potential new applications. Reported here is discovery of a series of new PDE5 inhibitors by structure-based design, molecular docking, chemical synthesis, and enzymatic characterization. The best compound, 3(4-hydroxybenzyl)-1-(thiophen-2-yl)chromeno[2,3-c]pyrrol-9(2H)-one (57), has an IC50 of 17 nM against the PDE5 catalytic domain and good selectivity over other PDE families. The crystal structure of the PDE5 catalytic domain in complex with 57 was determined at 2 angstrom resolution and showed that 57 occupies the same pocket as other PDE5 inhibitors, but has a different binding pattern in detail. On the basis of the binding pattern of 57, a novel scaffold can be proposed as a candidate of PDE inhibitors. (C) 2014 Elsevier Inc. All rights reserved.
• RANGACHARI K.; MAZUMDAR A. K. D.; BANERJI K. D., J. INDIAN CHEM. SOC., 1980, 57, NO 10, 1014-1016
  作者：RANGACHARI K.、 MAZUMDAR A. K. D.、 BANERJI K. D.

  DOI：——

  日期：——
• KULKARNI S. U.; THAKAR K. A., J. INDIAN CHEM. SOC. <JICS-AH>, 1976, 53, NO 3, 279-282
  作者：KULKARNI S. U.、 THAKAR K. A.

  DOI：——

  日期：——