(E)-1-(3-chlorophenyl)-3-(dimethylamino)prop-2-en-1-one | 876376-75-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-1-(3-chlorophenyl)-3-(dimethylamino)prop-2-en-1-one
• 英文别名: (2E)-1-(3-chlorophenyl)-3-(dimethylamino)prop-2-en-1-one
• CAS: 876376-75-9
• 化学式: C₁₁H₁₂ClNO
• 分子量: 209.675
• InChiKey: LDBZHHVGVAIVBT-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2924299090
• 储存条件：
  | 室温 |

SDS

MSDS英文版

反应信息

• 作为反应物：
  描述：

  (E)-1-(3-chlorophenyl)-3-(dimethylamino)prop-2-en-1-one 在 ammonium acetate 、 一水合肼 、 溶剂黄146 作用下， 生成 6-(3-chlorophenyl)-2-methylnicotinohydrazide
  参考文献：
  名称：

  Protective effect of novel substituted nicotine hydrazide analogues against hypoxic brain injury in neonatal rats via inhibition of caspase

  摘要：

  In hypoxic-ischemic injury of the brain of neonates, the level of caspase-3 was found to be aberrantly activated. Its overexpression leads to the alteration of cytoskeleton protein fodrin and loss of DNA repair enzyme which ultimately results in neurological impairment and disability. Concerning this, the present study was intended to develop novel nicotine hydrazide analogues as caspase inhibitors via efficient synthetic route. These compounds were subsequently tested for inhibitory activity against caspase-3 and -7 where they exhibit highly potent activity against caspase-3 revealing compound 5k as most potent inhibitor (IC50 = 19.4 +/- 2.5 mu M). In Western blot analysis, 5k considerably inhibits the overexpression of caspase-3. The aryl nicotinate of compound 5k, as indicated by molecular docking was found to engage His121 and critical enzyme thiols, i.e., Cys163 of caspase-3 for its potent activity. Moreover, histopathological examination of brain tissues and hippocampus neurons showed that compound 5k considerably improves the brain injury and exert neuroprotective effects in hypoxic-ischemic (HI). In brain homogenate, 5k significantly improves the activity of MDA, SOD, GSH-Px, CAT and T-AOC to exert its beneficial effect against oxidative stress induced by HI injury. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.04.031
• 作为产物：
  描述：

  对氯苯乙酮 在 N,N-二甲基甲酰胺二甲基缩醛 作用下， 生成 (E)-1-(3-chlorophenyl)-3-(dimethylamino)prop-2-en-1-one
  参考文献：
  名称：

  (Substituted-phenyl)-1,2,4-triazolo[4,3-a]-pyrimidines and

  摘要：

  这份披露描述了具有抗焦虑活性的取代的1,2,4-三氮唑[1,5-a]嘧啶和取代的1,2,4-三氮唑[4,3-a]嘧啶。

  公开号：

  US04209621A1

文献信息

• SUBSTITUTED PYRIDINYL-PYRIMIDINES AND THEIR USE AS MEDICAMENTS
  申请人：Dahmann Georg

  公开号：US20130023502A1

  公开（公告）日：2013-01-24

  The invention relates to new substituted pyridinyl-pyrimidines of formula 1 wherein ring A is a five-membered saturated or unsaturated carbocyclic ring which optionally comprises one, two or three heteroatoms each independently from each other selected from the group N, S and O, wherein R 1 , R 2 , R 4 , R 3 , R 5 and R 6 are defined as in claim 1 and wherein ring A is further optionally substituted by one or two further substituents and the pharmaceutically acceptable salts, diastereomers, enantiomers, racemates, hydrates and solvates of the aforementioned compounds.

  该发明涉及公式1中的新取代吡啶基嘧啶化合物， 其中环A是一个含有五个成员的饱和或不饱和碳环，该环可选地包含一个、两个或三个异原子，每个异原子独立地选自N、S和O组成， 其中R1、R2、R4、R3、R5和R6如权利要求书中所定义，并且环A进一步可选地被一个或两个进一步取代基取代，以及上述化合物的药用盐、二对映体、对映体、消旋体、水合物和溶剂化合物。
• Rh(III)-Catalyzed Enaminone-Directed C–H Coupling with α-Diazo-α-phosphonoacetate for Reactivity Discovery: Fluoride-Mediated Dephosphonation for C–C Coupling Reactions
  作者：Chao Song、Chen Yang、Hua Zeng、Wenjing Zhang、Shan Guo、Jin Zhu

  DOI：10.1021/acs.orglett.8b01406

  日期：2018.7.6

  Rh(III)-catalyzed enaminone-directed C–H coupling with α-diazo-α-phosphonoacetate has been used for the identification of fluoride-mediated dephosphonation C–C coupling reactivity for the synthesis of 4-hydroxy-1-naphthoates. Intermolecular C–C coupling of α-phosphonoacetate and benzaldehyde for (E)-selective α,β-unsaturated ester synthesis has also been achieved.

  Rh（III）催化的与α-重氮-α-膦酰基乙酸酯结合的烯胺酮定向的C–H偶联已用于鉴定氟化物介导的膦酰基化的C–C偶联反应，用于合成4-羟基-1-萘甲酸酯。还实现了α-膦酰基乙酸酯和苯甲醛的分子间CC偶联，用于（E）-选择性α，β-不饱和酯的合成。
• A Synthesis of Novel Pyrazolylthienopyrimidine Derivatives as IL-6/STAT3 Inhibitors
  作者：Sung Min Kim、Seung Woong Lee、Yang-Heon Song

  DOI：10.5012/bkcs.2014.35.9.2859

  日期：2014.9.20

  at the various conditions (catalyst, reaction temperature and solvent). When the same reaction was carried out in refluxing ethanol in the presence of 1 equiv HCl as a catalyst, 3Aa was obtained as a major product in optimum yield (65%, Table 1, entry 6) within 6 h. Next, as depicted in Table 2, the reaction of 1A with 2b-h Table 1. Optimization for the reaction of 1A with 2a

  白细胞介素 6 (IL-6) 作为与 TNF-α 和 IL-8 一起的促炎细胞因子，在炎症的诱导以及慢性炎症免疫反应的持续中起核心作用。并且，已经在几种疾病的炎症组织中发现了过量产生的 IL-6，例如类风湿性关节炎、牛皮癣、炎症性肠病、骨关节炎、多发性骨髓瘤，以及人类动脉粥样硬化斑块。IL-6 与其受体（IL-6R，一种配体结合的 80 kDa 糖蛋白链）结合并诱导信号转导糖蛋白 130 (gp130) 的同源二聚化，导致 Janus 激酶 (Jak)/信号转导器的激活和转录信号激活因子 3 (STAT3)。STAT3 在大多数肿瘤和癌症中也经常过度表达或持续激活，并且发现激活的 STAT3 可以抑制肿瘤免疫监视。因此，IL-6 刺激的 STAT3 激活通路的阻断可能是发现新药的有吸引力的治疗靶点，目前正在紧张研究中。另一方面，噻吩并嘧啶及其衍生物是一类最具生物活性的重要化合物，具有抗菌、
• Substituted-6H,8H-pyrimido-[1,2,3-cd]purine-8,10-(9H)-diones and
  申请人：American Cyanamid Company

  公开号：US04904658A1

  公开（公告）日：1990-02-27

  Substituted-6H,8H-pyrimido[1,2,3-cd]purine-8,10(9H)-diones and substituted-6H,10H-pyrimido[1,2-cd]purin-10-ones which are useful as cognition enhancing agents, anxiolytic agents and/or antihypertensive agents in the treatment of cognitive and relative neutral behavioral problems, anxiety and hypertension in mammals.

  Substituted-6H,8H-嘧啶并[1,2,3-cd]嘌呤-8,10(9H)-二酮和替代的6H,10H-嘧啶并[1,2-cd]嘌呤-10-酮，可用作改善认知、抗焦虑和/或降压剂，用于治疗哺乳动物的认知和相关神经行为问题、焦虑和高血压。
• Iodine-Catalyzed Cross Dehydrogenative Coupling Reaction: Sulfenylation of Enaminones Using Dimethyl Sulfoxide as an Oxidant
  作者：Yogesh Siddaraju、Kandikere Ramaiah Prabhu

  DOI：10.1021/acs.joc.7b00073

  日期：2017.3.17

  Synthesis of polyfunctionalized aminothioalkenes has been demonstrated using iodine as a catalyst (30 mol %) and dimethyl sulfoxide as an oxidant under metal-free reaction conditions. This methodology allows a facile sulfenylation of enaminones with a broad range of heterocyclic thiols and thiones using cross dehydrogenative coupling methods. In addition, this strategy is highly practical as it employs

  已经证明在无金属的反应条件下使用碘作为催化剂（30mol％）并且使用二甲基亚砜作为氧化剂来合成多官能化氨基硫代烯烃。该方法允许使用交叉脱氢偶联方法将烯胺酮与各种杂环硫醇和硫酮轻松进行亚磺酰基化。另外，该策略是高度实用的，因为它使用廉价且易于获得的碘和DMSO，且反应时间短。当前的方法学是最简单的方法之一，并且提供了通过交叉脱氢偶联方法对烯胺酮进行亚磺酰基化的直接方法。