5-(2-Bromoprop-2-enoylamino)-1-benzothiophene-2-carboxylic acid | 561318-70-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 5-(2-Bromoprop-2-enoylamino)-1-benzothiophene-2-carboxylic acid
• CAS: 561318-70-5
• 化学式: C₁₂H₈BrNO₃S
• 分子量: 326.17
• InChiKey: KAKPXSSJUZSHAY-UHFFFAOYSA-N

物化性质

• 熔点：
  190-195 °C
• 沸点：
  601.2±55.0 °C(Predicted)
• 密度：
  1.780±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  94.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(2-Bromoprop-2-enoylamino)-1-benzothiophene-2-carboxylic acid 在 盐酸 、 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 乙酸乙酯 为溶剂， 反应 28.0h， 生成 5-(2-Bromo-acryloylamino)-benzo[b]thiophene-2-carboxylic acid (2-amino-ethyl)-amide
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Hybrid Molecules Containing α-Methylene-γ-Butyrolactones and α-Bromoacryloyl Moieties

  摘要：

  The synthesis and biological activity of hybrids 8-18 prepared combining alpha-methylene-gamma-butyrolactones and alpha-bromoacryloylamides have been described and their structure -activity relationships discussed. All these heterobifunctional compounds demonstrate good antileukemic activity, significantly superior to that of both alkylating units alone. Using the human leukemia HL-60 cell line, selected compounds 10, 11, 13, and 17 were found to induce morphological changes and internucleosomal DNA fragmentation characteristic of apoptotic cell death.

  DOI：

  10.1021/jm058012o
• 作为产物：
  描述：

  5-硝基-1-苯并噻吩-2-羧酸 在 palladium on activated charcoal 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N'-羰基二咪唑 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、379.21 kPa 条件下， 反应 24.0h， 生成 5-(2-Bromoprop-2-enoylamino)-1-benzothiophene-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and growth inhibition activity of α-Bromoacrylic heterocyclic and benzoheterocyclic derivatives of distamycin A modified on the amidino moiety

  摘要：

  The design, synthesis and in vitro activities of novel alpha-bromoacryloyl pyrazole, imidazole and benzoheterocyclic derivatives of distamycin A, in which the amidino moiety has been replaced by moieties of different physico-chemical features are described, and the structure-activity relationships are discussed. In spite of the relevance of these modifications on the distamycin frame, these derivatives showed significant growth inhibitory activity against mouse leukemia L1210 cells. Therefore, the presence of the amidino moiety, and in general of a basic moiety, is not an absolute requirement for biological activity of alpha-bromoacrylic derivatives of distamycin. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00533-3

文献信息

• Hybrid molecules containing benzo[4,5]imidazo[1,2-d][1,2,4]thiadiazole and α-bromoacryloyl moieties as potent apoptosis inducers on human myeloid leukaemia cells
  作者：Romeo Romagnoli、Pier Giovanni Baraldi、Maria Dora Carrion、Olga Cruz-Lopez、Delia Preti、Mojgan Aghazadeh Tabrizi、Francesca Fruttarolo、Jörg Heilmann、Jaime Bermejo、Francisco Estévez

  DOI：10.1016/j.bmcl.2007.02.048

  日期：2007.5

  The synthesis and biological activity of a series of hybrids 1-5 prepared combining a benzo[4,5]imidazo[1,2-d][1,2,4]thiadiazole and different benzoheterocyclic alpha-bromoacryloyl amides have been described and their structure-activity relationships discussed. All these hetero-bifunctional compounds were highly cytotoxic against the human myeloid leukaemia cell lines HL-60 and U937 (IC50 0.24-1.72 mu M), significantly superior to that of both alkylating units alone. In human myeloid leukaemia HL-60 cells we observed that these compounds suppress survival and proliferation by triggering morphological changes and internucleosomal DNA fragmentation characteristic of apoptotic cell death. The apoptosis induced by these compounds is mediated by caspase-3 activation and is also associated to an early release of cytochrome c from the mitochondria. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis and biological activity of alpha-bromoacryloyl lexitropsin conjugates
  作者：Romeo Romagnoli、Pier Giovanni Baraldi、Maria Antonietta Iaconinoto、Maria Dora Carrion、Mojgan Aghazadeh Tabrizi、Roberto Gambari、Monica Borgatti、Jörg Heilmann

  DOI：10.1016/j.ejmech.2005.05.003

  日期：2005.11

  The design, synthesis and biological evaluation of lexitropsins bearing mixed heterocyclic and benzoheterocyclic moieties and tethered to an alpha-bromo acrylic moiety acting as alkylating moiety are reported, and structure-activity relationships determined. With respect to anti proliferative activity against L1210 and K562 cells, compounds 7 and 10 showed the greatest potency, while compounds 4 and 5 exhibit the lowest activity. Among the synthesized compounds 4-12, the derivative 10 was found to be the most potent member of this class and it is 70-fold more active than the bis-pyrrole counterpart 3 against L1210 cell line. In addition, the cytotoxicity of derivatives 5-12 against KB cells and the influence of different glutathione (GSH) concentrations on the cytotoxic effects was also investigated. (c) 2005 Elsevier SAS. All rights reserved.
• BENZOHETEROCYCLIC DISTAMYCIN DERIVATIVES, PROCESS FOR PREPARING THEM, AND THEIR USE AS ANTITUMOR AND ANTIVIRAL AGENTS
  申请人：Pharmacia Italia S.p.A.

  公开号：EP0937070B1

  公开（公告）日：2003-12-03
• BENZOHETEROCYCLIC DISTAMYCIN DERIVATIVES, PROCESS FOR PREPARING THEM, AND THEIR USE AS ANTITUMOR AGENTS
  申请人：PHARMACIA & UPJOHN S.p.A.

  公开号：EP1064281A1

  公开（公告）日：2001-01-03
• US6153642A
  申请人：——

  公开号：US6153642A

  公开（公告）日：2000-11-28