(E)-3-(5-nitrothiophen-2-yl)acryloyl chloride | 55785-89-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: (E)-3-(5-nitrothiophen-2-yl)acryloyl chloride
• 英文别名: (E)-3-(5-nitrothiophen-2-yl)prop-2-enoyl chloride
• CAS: 55785-89-2
• 化学式: C₇H₄ClNO₃S
• 分子量: 217.633
• InChiKey: XUQKFBOIGOWKHU-HNQUOIGGSA-N

物化性质

• 沸点：
  358.1±32.0 °C(Predicted)
• 密度：
  1.551±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.43
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.21
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (E)-3-(5-nitrothiophen-2-yl)acryloyl chloride 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 8.5h， 生成 (E)-3-(2-nitrothiophene-5-yl)-N-(oxiranylmethyl)propenamide
  参考文献：
  名称：

  Synthesis of a series of nitrothiophenes with basic or electrophilic substituents and evaluation as radiosensitizers and as bioreductively activated cytotoxins

  摘要：

  A series of 2- and 3-nitrothiophene-5-carboxamides bearing N-(omega-aminoalkyl) side chains has been prepared by treatment of the thiophenecarbonyl chloride with the appropriate (protected) omega-aminoalkylamine. Analogous N-(oxiranylmethyl)nitrothiophene-5-carboxamides have been synthesized by epoxidation of the corresponding N-allylamide. Compounds in both classes were evaluated in vitro both as radiosensitizers of hypoxic mammalian cells and as selective bioreductively activated cytotoxins. The most potent radiosensitizers were those agents with strong tertiary amine bases or oxiranes in the side chain. Studies in vivo showed that 2-methyl-N-[2-(dimethylamino)ethyl]-3-nitrothiophene-5-carboxamide caused slight radiosensitization of the KHT sarcoma in mice given 0.34 mmol kg-1. However, administration of this and related tertiary amines at higher doses was precluded by systemic toxicity.

  DOI：

  10.1021/jm00111a029
• 作为产物：
  描述：

  3-(5-硝基-2-噻吩)丙烯酸 在 氯化亚砜 作用下， 以 甲苯 为溶剂， 生成 (E)-3-(5-nitrothiophen-2-yl)acryloyl chloride
  参考文献：
  名称：

  稠合杂环MLKL抑制剂的设计、合成及其抗坏死性凋亡活性

  摘要：

  坏死性凋亡是程序性细胞死亡 (PCD) 的一种重要形式，由死亡受体介导且独立于 caspase 蛋白水解酶。混合谱系激酶结构域样（MLKL）是坏死性凋亡的最终效应器，在坏死性凋亡的执行中发挥着不可替代的作用。然而，MLKL抑制剂的研究还处于起步阶段。 Necrosulfonamide (NSA) 是一种早期发现的共价 MLKL 抑制剂，具有中等抗坏死性凋亡活性和尚未广泛披露的构效关系 (SAR)。在本研究中，在保留共价基序的情况下，我们旨在通过引入末端稠合杂环并同时揭示部分的SAR来提高活性。结果，化合物 和 通过与 MLKL 共价结合而在类似物中表现出最佳的抗坏死性凋亡活性（EC = 148.4 和 595.9 nM）。特区政府的成立也是为了指导该领域的进一步结构优化。

  DOI：

  10.1016/j.bmc.2024.117659

文献信息

• Activity-based protein profiling reveals GSTO1 as the covalent target of piperlongumine and a promising target for combination therapy for cancer
  作者：Li Li、Yue Zhao、Ran Cao、Lin Li、Gaihong Cai、Jiaojiao Li、Xiangbing Qi、She Chen、Zhiyuan Zhang

  DOI：10.1039/c9cc00917e

  日期：——

  Through ABPP, piperlongumine was identified to induce cancer cell death by covalently binding and inhibiting GSTO1 and has a broad spectrum synergistic effect with other anti-cancer agents.

  通过ABPP，已确定piperlongumine通过共价结合和抑制GSTO1诱导癌细胞死亡，并与其他抗癌药物具有广谱协同作用。
• Capsaicin derivatives with nitrothiophene substituents: Design, synthesis and antibacterial activity against multidrug-resistant S. aureus
  作者：Zhi-Cheng Wang、Bingyan Wei、Fang-Ning Pei、Teng Yang、Jie Tang、Song Yang、Li-Fang Yu、Cai-Guang Yang、Fan Yang

  DOI：10.1016/j.ejmech.2020.112352

  日期：2020.7

  To address the emergency caused by multi-drug resistant Staphylococcus aureus, a series of novel capsaicin derivatives with nitrothiophene substituents have been designed and evaluated for the antibacterial activities against S. aureus Newman and multidrug-resistant strains (NRS-1, NRS-70, NRS-100, NRS-108, and NRS-271). The structure-activity relationship was further revealed. Compound 13c, 13f, and

  为了解决由多药耐药金黄色葡萄球菌引起的紧急情况，已设计了一系列具有硝基噻吩取代基的新型辣椒素衍生物，并评估了其对金黄色葡萄球菌纽曼菌和多药耐药菌株（NRS-1，NRS-70， NRS-100，NRS-108和NRS-271）。构效关系得到进一步揭示。化合物13c，13f和13g对葡萄球菌的生长具有高活性，最小抑菌浓度（MIC）值为0.39-1.56μg/ mL。恶二唑衍生的化合物21（酯13f的生物甾醇）是MIC值为0.20-0.78μg/ mL的5种具有多重耐药性的金黄色葡萄球菌菌株抗生长的最有效候选者，与体外万古霉素相比，其活性更高。值得注意的是
• Synthesis and in vitro antitrypanosomal activity of novel Nifurtimox analogues
  作者：Rocío Pozas、Javier Carballo、Clementina Castro、Julieta Rubio

  DOI：10.1016/j.bmcl.2005.01.002

  日期：2005.3

  Eight novel analogues of Nifurtimox, 4-[(5-nitrofurfurylidene)amino]-3-methylthiomorpholine-1,1-dioxide, containing alpha-beta unsaturated amides, were synthesized and evaluated for their in vitro activity against Trypanosoma cruzi epimastigotes. Four derivatives bearing a nitro group at the 5-position of the furan ring were the most active in inhibiting culture growth and provoking cell death, showing

  合成了八种新型的呋喃酮氮类似物，即4-[（（5-硝基糠基亚氨基）氨基] -3-甲基硫代吗啉-1,1-二氧化物，含有α-β不饱和酰胺，并评估了它们对克鲁斯锥虫的体外活性。在呋喃环5位上带有硝基的四种衍生物在抑制培养物生长和引起细胞死亡方面最活跃，其锥虫杀伤活性超过了我们的阳性对照Nifurtimox的效力的三倍。缺少硝基的两种衍生物的效力低于阳性对照。活性硝基衍生物非常有效地导致淫前鞭毛虫死亡，这表明硝基还原的作用机理。
• Large Second‐Order NLO Activity in Poly(4‐vinylpyridine) Grafted with Pd ^II and Cu ^II Chromophoric Complexes with Tridentate Bent Ligands Containing Heterocycles
  作者：Fabio Borbone、Antonio Carella、Ugo Caruso、Giuseppina Roviello、Angela Tuzi、Principia Dardano、Stefano Lettieri、Pasqualino Maddalena、Alberto Barsella

  DOI：10.1002/ejic.200701171

  日期：2008.4

  Two N-salicylidene-N'-acylhydrazines tridentate ligands containing heterocycles were prepared and utilized for the synthesis of mononuclear acentric complexes of Cu-II and Pd-II and pyridine serves as an additional ligand ((MLPy)-Py-x, M = metal, L-x = li

  制备了两个含有杂环的 N-水杨基-N'-酰基肼三齿配体，用于合成 Cu-II 和 Pd-II 的单核无着丝粒配合物，吡啶作为额外的配体 ((MLPy)-Py-x, M =金属，Lx = li
• Necrosulfonamide inhibits necroptosis by selectively targeting the mixed lineage kinase domain-like protein
  作者：Daohong Liao、Liming Sun、Weilong Liu、Sudan He、Xiaodong Wang、Xiaoguang Lei

  DOI：10.1039/c3md00278k

  日期：——

  Through high-throughput screening of 200 000 compounds and subsequent structure–activity relationship (SAR) studies we identified necrosulfonamide (NSA) as a potent small molecule inhibitor for necroptosis, induced by a combination of TNF-a, Smac mimetic, and z-VAD-fmk (T/S/Z).

  通过对20万种化合物进行高通量筛选和随后的结构活性关系（SAR）研究，我们确定了硫酰胺（NSA）作为一种有效的小分子抑制剂，用于由TNF-a、Smac模拟剂和z-VAD-fmk（T/S/Z）组合诱导的坏死程序。