N-(but-3-en-1-yl)acrylamide | 1415686-28-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(but-3-en-1-yl)acrylamide
• 英文别名: N-but-3-enylprop-2-enamide
• CAS: 1415686-28-0
• 化学式: C₇H₁₁NO
• 分子量: 125.17
• InChiKey: WDSRHHTXYKFXPX-UHFFFAOYSA-N

物化性质

• 沸点：
  252.1±23.0 °C(Predicted)
• 密度：
  0.892±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(but-3-en-1-yl)acrylamide 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 正丁基锂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.75h， 生成 1-cinnamoyl-5,6-dihydropyridin-2(1H)-one
  参考文献：
  名称：

  Piperlongumine (piplartine) and analogues: Antiproliferative microtubule-destabilising agents

  摘要：

  Piperlongumine (piplartine, 1) is a small molecule alkaloid that is receiving intense interest due to its antiproliferative and anticancer activities. We investigated the effects of 1 on tubulin and microtubules. Using both an isolated tubulin assay, and a combination of sedimentation and western blotting, we demonstrated that 1 is a tubulin-destabilising agent. This result was confirmed by immunofluorescence and confocal microscopy, which showed that microtubules in MCF-7 breast cancer cells were depolymerized when treated with 1. We synthesised a number of analogues of 1 to explore structure-activity relationships. Compound 13 had the best cytotoxic profile of this series, showing potent effects in human breast carcinoma MCF-7 cells whilst being relatively non-toxic to non-tumorigenic MCF-10a cells. These compounds will be further developed as potential clinical candidates for the treatment of breast cancer. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.09.048
• 作为产物：
  描述：

  3-丁烯-1-胺 、 丙烯酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以80%的产率得到N-(but-3-en-1-yl)acrylamide
  参考文献：
  名称：

  作为有效醛糖还原酶抑制剂 (ARI) 的新 piplartine 类似物的合成和生物学评价

  摘要：

  作为我们致力于从天然来源开发抗糖尿病药物的继续努力，从胡椒中分离出了哌拉汀，并发现它可以抑制重组人 ALR2，IC 50为 160 μM。为了提高功效，通过修饰这种天然产物先导物的苯乙烯基/芳香族和杂环官能团，合成了一系列类似物。对所有衍生物的ALR2抑制活性进行了测试，结果表明，哌拉汀与吲哚衍生物迈克尔加成制备的加合物3c 、 3e和2j表现出有效的ARI活性，而其他化合物则表现出不同程度的抑制作用。这些活性化合物还能够防止山梨醇在人红细胞中积聚。

  DOI：

  10.1016/j.ejmech.2012.09.014

文献信息

• 苯丙烯酰胺衍生物及其制备方法和医药用途
  申请人：安徽省逸欣铭医药科技有限公司

  公开号：CN106432189A

  公开（公告）日：2017-02-22

  本发明属于药物化学及医药技术领域，公开了一种苯丙烯酰胺衍生物（Ⅰ）和（Ⅱ）、其制备方法和医药用途。该新化合物具体显著的抗血小板聚集活性，为血栓栓塞性疾病患者提供了新的候选药物。
• A facile approach to α,β-unsaturated lactams by ring-closing metathesis
  作者：Humaira Yasmeen Gondal、Didier Buisson

  DOI：10.1007/s10593-016-1858-y

  日期：2016.3

  A facile and efficient strategy for the synthesis of α,β-unsaturated lactams through ring-closing metathesis of easily prepared diene amides is being reported here. Reaction conditions were optimized for metathetic cyclization of diene amides to obtain five- to sevenmembered unsubstituted and β-substituted α,β-unsaturated lactams in good to excellent yield.

  在此报道了通过容易制备的二烯酰胺的闭环易位合成α，β-不饱和内酰胺的简便有效的策略。优化了反应条件以使二烯酰胺进行易位环化，以良好至极好的收率获得五元至七元的未取代和β-取代的α，β-不饱和内酰胺。
• Crosslinkable or functionalizable polymers for 3D printing of soft materials
  申请人：University of Florida Research Foundation, Inc.

  公开号：US10814605B2

  公开（公告）日：2020-10-27

  Described herein are embodiments of compositions and methods relating to three-dimensional (3D) printing. Some embodiments are directed to a composition comprising a polymer with one or more dormant functional groups. According to some embodiments, the polymer may be formed through a controlled radical polymerization method. Some embodiments are directed to a composition comprising a polymer with one or more pendent crosslinkable groups. In some cases, the composition may be used as an “ink” for 3D printing. For example, the composition may be injected into a medium. The composition and/or medium may, in some embodiments, further comprise an initiator and/or a crosslinker. After injection of the composition into the medium, the one or more dormant functional groups and/or one or more pendent crosslinkable groups may be activated, and the polymer may be crosslinked. In certain cases, the crosslinked polymer may be removed from the medium to produce a freestanding three-dimensional structure.

  本文描述的是与三维（3D）打印有关的组合物和方法的实施例。一些实施例涉及一种组合物，该组合物包含具有一个或多个休眠官能团的聚合物。根据某些实施例，聚合物可通过受控自由基聚合方法形成。一些实施例涉及一种组合物，该组合物包含具有一个或多个可悬垂交联基团的聚合物。在某些情况下，该组合物可用作 3D 打印的 "墨水"。例如，可将组合物注入介质中。在某些实施例中，组合物和/或介质可进一步包含引发剂和/或交联剂。将组合物注入介质后，一个或多个休眠官能团和/或一个或多个悬垂可交联基团可被激活，聚合物可被交联。在某些情况下，可将交联聚合物从介质中移除，以产生独立的三维结构。
• Design and synthesis of benzylidenecyclohexenones as TrxR inhibitors displaying high anticancer activity and inducing ROS, apoptosis, and autophagy
  作者：Jianqiang Qian、Zhongyuan Xu、Chi Meng、Ji Liu、Pei-Ling Hsu、Yangyang Li、Weizhong Zhu、Yumin Yang、Susan L. Morris-Natschke、Kuo-Hsiung Lee、Yanan Zhang、Yong Ling

  DOI：10.1016/j.ejmech.2020.112610

  日期：2020.10

  Oxidative therapy, a strategy that specifically increases reactive oxygen species (ROS) levels in tumor cells by disrupting the redox homeostasis has gained increasing interest. The antitumor effects of the natural product piperlongumine (PL) appear to result from its ability to increase intracellular ROS levels via inhibition of antioxidative thioredoxin reductase (TrxR). Twenty-seven benzylidenecyclohexenone-based PL analogues (2a-v and 15a-e) were designed, synthesized and evaluated for their pharmacological properties. Most of the compounds exhibited potent antiproliferative activities against five human cancer cell lines, especially against breast tumor cells. One of the most promising analogueues 2c showed 12-fold higher inhibitory activity against the thioredoxin reductase (TrxR) than PL and surpressed the expression of TrxR1 protein in breast cancer cells and inhibited TrxR enzymatic activity. In addition, 2c increased ROS levels and resulted in marked apoptosis by regulating apoptosis-related proteins expressed in the breast cancer cells. Compound 2c also triggered the formation of autophagosomes and autolysosomes by promoting the expression of LC3-II and Beclin-1 and diminishing the expression of LC3-I and p62 proteins. Finally, 2c displayed low acute toxicity and good inhibitory potency to tumors in mice. Overall, 2c is a promising anti-breast cancer candidate warranting further investigation. (C) 2020 Elsevier Masson SAS. All rights reserved.
• Design and synthesis of a C7-aryl piperlongumine derivative with potent antimicrotubule and mutant p53-reactivating properties
  作者：Surendra R. Punganuru、Hanumantha Rao Madala、Sanjay N. Venugopal、Ramakrishna Samala、Constantinos Mikelis、Kalkunte S. Srivenugopal

  DOI：10.1016/j.ejmech.2015.10.052

  日期：2016.1

  Small molecules that can restore biological function to the p53 mutants found in human cancers have been highly sought to increase the anticancer efficacy. In efforts to generate hybrid anticancer drugs that can impact two or more targets simultaneously, we designed and developed piperlongumine (PL) derivatives with an aryl group inserted at the C-7 position. This insertion bestowed a combretastatin A4 (CA4, an established microtubule disruptor) like structure while retaining the piperlongumine configuration. The new compounds exhibited potent antiproliferative activities against eight cancer cell lines, in particular, were more cytotoxic against the SKBR-3 breast cancer cells which harbor a R175H mutation in p53 suppressor. KSS-9, a representative aryl PL chosen for further studies induced abundant ROS generation and protein glutathionylation. KSS-9 strongly disrupted the tubulin polymerization in vitro, destabilized the microtubules in cells and induced a potent G2/M cell cycle block. More interestingly, KSS-9 showed the ability to reactivate the p53 mutation and restore biological activity to the R175H mutant protein present in SKBR3 cells. Several procedures, including immunocytochemistry using conformation-specific antibodies for p53, immunoprecipitation combined with western blotting, electrophoretic shift mobility shift assays showed a reciprocal loss of mutant protein and generation of wildtype like protein. p53 reactivation was accompanied by the induction of the target genes, MDM2, p21cip1 and PUMA. Mechanistically, the redox-perturbation in cancer cells by the hybrid drug appears to underlie the p53 reactivation process. This anticancer drug approach merits further development. (C) 2015 Elsevier Masson SAS. All rights reserved.