3-[(2E)-3-(5-bromo-2-thienyl)prop-2-enoyl]-4-hydroxy-6-methyl-2H-pyran-2-one | 369389-42-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-[(2E)-3-(5-bromo-2-thienyl)prop-2-enoyl]-4-hydroxy-6-methyl-2H-pyran-2-one
• 英文别名: 3-[(E)-3-(5-bromo-thien-2-yl)-acryloyl]-4-hydroxy-6-methyl-pyran-2-one；3-[(E)-3-(5-bromo-2-thienyl)prop-2-enoyl]-4-hydroxy-6-methyl-pyran-2-one；3-[(E)-3-(5-bromothiophen-2-yl)prop-2-enoyl]-4-hydroxy-6-methylpyran-2-one
• CAS: 369389-42-4
• 化学式: C₁₃H₉BrO₄S
• 分子量: 341.182
• InChiKey: WFUKGGYKYBUUJK-DUXPYHPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  91.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-[(2E)-3-(5-bromo-2-thienyl)prop-2-enoyl]-4-hydroxy-6-methyl-2H-pyran-2-one 生成 3-[7-(5-bromo-thien-2-yl)-2,3,6,7-tetrahydro-[ 1,4]thiazepin-5-yl]-4-hydroxy-6-methyl-pyran-2-one 、 3-[7-(1-benzenesulfonyl-1H-pyrrol-2-yl)-2,3,6,7-tetrahydro-[1,4]thiazepin-5-yl]-4-hydroxy-6-methyl-pyran-2-one
  参考文献：
  名称：

  Substituted 1, 4-thiazepine and analogs as activators of caspases and inducers of apoptosis and the use thereof

  摘要：

  本发明涉及被一般式I表示的取代的1,4-噻吩和其类似物，其中虚线、A1、A2、A3、X1和R1在此处被定义。本发明还涉及发现具有式I的化合物是卡泊酶激活剂和凋亡诱导剂。因此，本发明的卡泊酶激活剂和凋亡诱导剂可用于诱导在各种临床病况中发生细胞死亡，其中异常细胞的不受控制的生长和扩散。

  公开号：

  US20020010169A1
• 作为产物：
  描述：

  3-[(2E)-3-(4-bromo-2-thienyl)prop-2-enoyl]-6-methyl-2-oxo-2H-pyran-4-yl difluoridoborate 在 水 、 sodium carbonate 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 以76%的产率得到3-[(2E)-3-(5-bromo-2-thienyl)prop-2-enoyl]-4-hydroxy-6-methyl-2H-pyran-2-one
  参考文献：
  名称：

  Discovery of 3-acetyl-4-hydroxy-2-pyranone derivatives and their difluoridoborate complexes as a novel class of HIV-1 integrase Inhibitors

  摘要：

  HIV-1 integrase (IN) has emerged as an important therapeutic target for anti-HIV drug development. Its uniqueness to the virus and its critical role in the viral life cycle makes IN suitable for selective inhibition. The recent approval of Raltegravir (MK-0518) has created a surge in interest and great optimism in the field. In our ongoing IN drug design research, we herein report the discovery of substituted analogs of 3-acetyl-4-hydroxy-2-pyranones and their difluoridoborate complexes as novel IN inhibitors. In many of these compounds, complexation with boron difluoride increased the potency and selectivity of IN inhibition. Compound 9 was most active with an IC50 value of 9 mu M and 3 mu M for 3'-processing and strand transfer inhibition, respectively. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.067

文献信息

• SUBSTITUTED 1,4-THIAZEPINE AND ANALOGS AS ACTIVATORS OF CASPASES AND INDUCERS OF APOPTOSIS AND THE USE THEREOF
  申请人：Cytovia, Inc.

  公开号：EP1324993A2

  公开（公告）日：2003-07-09
• US6861419B2
  申请人：——

  公开号：US6861419B2

  公开（公告）日：2005-03-01
• [EN] SUBSTITUTED 1,4-THIAZEPINE AND ANALOGS AS ACTIVATORS OF CASPASES AND INDUCERS OF APOPTOSIS AND THE USE THEREOF<br/>[FR] THIAZEPINE-1,4 SUBSTITUEE ET ANALOGUES DE CELLE-CI ACTIVATEURS DE CASPASES ET INDUCTEURS D'APOPTOSE, ET UTILISATION
  申请人：CYTOVIA INC

  公开号：WO2001079187A2

  公开（公告）日：2001-10-25

  The present invention is directed to substituted 1,4-thiazepine and analogs thereof, represented by the general Formula (I): wherein the dashed lines, A?1, A2, A3, X1 and R1¿ are defined herein. The present invention also relates to the discovery that compounds having Formula I are activators of capases and inducers of apoptosis. Therefore, the activators of caspases and inducers of caspases and inducers of apoptosis of this invention can be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.