3,5-bis(2-bromobenzylidene)-4-piperidone | 1353858-19-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3,5-bis(2-bromobenzylidene)-4-piperidone
• 英文别名: 3,5-Bis[(2-bromophenyl)methylidene]piperidin-4-one；3,5-bis[(2-bromophenyl)methylidene]piperidin-4-one
• CAS: 1353858-19-1
• 化学式: C₁₉H₁₅Br₂NO
• 分子量: 433.142
• InChiKey: SRIXJFUIIDOCNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  11H-茚并[1,2-b]喹喔啉-11-酮 、 L-苯丙氨酸 、 3,5-bis(2-bromobenzylidene)-4-piperidone 生成
  参考文献：
  名称：

  用于合成功能化螺茚[1,2-b]喹喔啉杂环杂化物的多米诺多组分方法及其抗菌活性、协同效应和分子对接模拟

  摘要：

  通过多米诺多组分 1,3-偶极环加成策略，使用离子液体中的新型偶氮甲碱叶立德，开发了一种迄今为止尚未探索的新型杂环化合物的便利合成，包括二螺吡咯烷、N-苯乙烯基哌啶酮和茚并 [1,2-b] 喹喔啉单元， 1-丁基-3-甲基咪唑鎓溴化物。该多米诺协议涉及 1,3-偶极环加成和伴随的烯胺反应，在一个步骤中以中等至良好的产率提供二螺吡咯烷系留的 N-苯乙烯基哌啶酮杂环。评估了这些化合物对细菌和真菌病原体的抗微生物活性，其中化合物 8f、8h 和 8l 对测试的微生物病原体显示出显着的活性。

  DOI：

  10.3390/molecules24101962
• 作为产物：
  描述：

  3,5-bis(2-bromobenzylidene)-4-piperidone hydrochloride 在 potassium carbonate 作用下， 以1.6 g的产率得到3,5-bis(2-bromobenzylidene)-4-piperidone
  参考文献：
  名称：

  CLEFMA—An anti-proliferative curcuminoid from structure–activity relationship studies on 3,5-bis(benzylidene)-4-piperidones

  摘要：

  3,5-Bis(benzylidene)-4-piperidones are being advanced as synthetic analogs of curcumin for anti-cancer and anti-inflammatory properties. We performed structure-activity relationship studies, by testing several synthesized 3,5-bis(benzylidene)-4-piperidones for anti-proliferative activity in lung adenocarcinoma H441 cells. Compared to the lead compound 1, or 3,5-bis(2-fluorobenzylidene)-4-piperidone, five compounds were found to be more potent (IC50 <30 mu M), and 16 compounds possessed reduced cell-killing efficacy (IC50 >50 mu M). Based on the observations, we synthesized 4-[3,5-bis(2-chlorobenzyl-idene-4-oxo-piperidine-1-yl)-4-oxo-2-butenoic acid] (29 or CLEFMA) as a novel analog of 1. CLEFMA was evaluated for anti-proliferative activity in H441 cells, and was found to be several folds more potent than compound 1. We did not find apoptotic cell population in flow cytometry, and the absence of apoptosis was confirmed by the lack of caspase cleavage. The electron microscopy of H441cells indicated that CLEFMA and compound 1 induce autophagic cell death that was inhibited by specific autophagy inhibitor 3-methyladenine. The results suggest that the potent and novel curcuminoid, CLEFMA, offers an alternative mode of cell death in apoptosis-resistant cancers. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.055

文献信息

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  DOI：10.2147/dddt.s133172

  日期：——

  Given the important role that inhibitory kappa B (IκB) kinase β (IKKβ) plays in pancreatic cancer (PC) development and progression, inhibitors targeting IKKβ are believed to be increasingly popular as novel anti-PC therapies. Two synthetic molecules, named EF24 and EF31, exhibited favorable potential in terms of inhibition of both IKKβ activity and PC cell proliferation. Aiming to enhance their cellular

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  DOI：10.1016/j.tetlet.2018.07.051

  日期：2018.8

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  DOI：10.1016/j.ejmech.2018.04.060

  日期：2018.5

  Stereoselective synthesis of a small library of novel spiroheterocyclic hybrids including indolizine, oxindole, and substituted piperidine units has been accomplished in [bmim]Br using a [3 + 2] cycloaddition strategy in good yield and were tested for their anti-inflammatory activities. The effects of compounds (4a-o) against inflammation were studied using carrageenan-induced hind paw oedema, croton

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• Discovery of diazahexa/hepta cyclic cage-like compounds with broad-spectrum antifungal activity against <i>Candida</i> and <i>Cryptococcus</i> species
  作者：Anthony Weinstock、Natarajan Arumugam、Abdulrahman I. Almansour、Raju Suresh Kumar、Shankar Thangamani

  DOI：10.1039/c9ra05777c

  日期：——

  FDA-approved antifungal drugs along with the paucity of antifungal drugs warrants novel drugs to treat invasive fungal infections. In this study, we investigated the antifungal activity of a novel series of diazahexa/hepta cyclic cage-like compounds. Results indicate that compounds with unsubstituted and o-methyl substitution on aryl rings exhibit potent broad-spectrum antifungal activity against various

  由念珠菌和隐球菌引起的侵袭性真菌感染会导致免疫功能低下的个体发生危及生命的感染。此外，对 FDA 批准的抗真菌药物耐药的真菌菌株的发生率增加以及抗真菌药物的缺乏需要新的药物来治疗侵袭性真菌感染。在这项研究中，我们研究了一系列新型二氮杂六/七环状笼状化合物的抗真菌活性。结果表明，在芳环上具有未取代和邻甲基取代的化合物对各种真菌菌株表现出有效的广谱抗真菌活性。此外，这些化合物对念珠菌表现出显着的抑制活性菌丝和生物膜的形成。总的来说，这项研究的结果表明，这些化合物有希望开发为治疗耐药真菌感染的新型抗真菌药物。
• Dispiropyrrolidine tethered piperidone heterocyclic hybrids with broad-spectrum antifungal activity against Candida albicans and Cryptococcus neoformans
  作者：Sarah Lawson、Natarajan Arumugam、Abdulrahman I. Almansour、Raju Suresh Kumar、Shankar Thangamani

  DOI：10.1016/j.bioorg.2020.103865

  日期：2020.7

  Invasive fungal infections along with rising incidence of resistance to antifungal drugs pose increasing threat to immunocompromised individuals, including cancer patients. In this study, we examined the antifungal activity of dispiropyrrolidine tethered piperidone heterocyclic hybrids. Results indicate that compounds 5a and 6i have demonstrated a potent antifungal effect on multiple fungal strains, including Candida albicans, without exhibiting cytotoxicity to mammalian cells. Furthermore, these two compounds exhibited significant inhibition on Candida albicans hyphae and biofilm development that surpasses the FDA-approved antifungal drug currently used for treatment. Taken together, our results suggest that 5a and 6i are promising candidates for development into new antifungal drugs.