<1-(acetylamino)-2,2-dichlorovinyl>triphenylphosphonium chloride | 76621-88-0

• 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: <1-(acetylamino)-2,2-dichlorovinyl>triphenylphosphonium chloride
• 英文别名: (1-acetylamino-2,2-dichloro-vinyl)-triphenyl-phosphonium; chloride；(1Z)-N-(2,2-dichloro-1-triphenylphosphaniumylethenyl)ethanimidate;hydrochloride
• CAS: 76621-88-0
• 化学式: C₂₂H₁₉Cl₂NOP*Cl
• 分子量: 450.732
• InChiKey: YQACJOJZVNOTOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.72
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  <1-(acetylamino)-2,2-dichlorovinyl>triphenylphosphonium chloride 在 sodium sulfide 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 (2-methyl-5-thioxo-2-oxazolin-4-ylidene)triphenylphosphorane
  参考文献：
  名称：

  Brovarets, V. S.; Lobanov, O. P.; Drach, B. S., Journal of general chemistry of the USSR, 1983, vol. 53, # 3, p. 574 - 577

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(1,2,2,2-四氯乙基)乙酰胺 、 三苯基膦 以 苯 为溶剂， 反应 3.0h， 以81%的产率得到<1-(acetylamino)-2,2-dichlorovinyl>triphenylphosphonium chloride
  参考文献：
  名称：

  Brovarets, V. S.; Lobanov, O.P.; Drach, B. S., Journal of general chemistry of the USSR, 1983, vol. 53, # 9, p. 1819 - 1823

  摘要：

  DOI：

文献信息

• Interaction of 1-acylamino-2,2-dichloroethenyl(triphenyl)phosphonium chlorides with alkanolamines
  作者：O. V. Golovchenko、E. R. Abdurakhmanova、S. O. Vladimirov、M. Y. Brusnakov、T. O. Krupoder、V. V. Sukhoveev、E. B. Rusanov、R. N. Vydzhak、V. S. Brovarets

  DOI：10.1080/10426507.2020.1759062

  日期：2020.10.2

  Abstract It is shown that the interaction of 1-acylamino-2,2-dichloroethenyl(triphenyl)-phosphonium chlorides with alkanolamines having a primary amino group results in the formation of 4-oxazolylphosphonium salts containing hydroxyalkylamine substituents at position 5 of the oxazole cycle. Under similar conditions the reaction of N-substituted alkanolamines with 1-acylamino-2,2-dichloroethenyl-(t

  摘要 研究表明，1-酰氨基-2,2-二氯乙烯（三苯基）氯化鏻与具有伯氨基的链烷醇胺的相互作用导致在恶唑环的 5 位形成含有羟烷基胺取代基的 4-恶唑基鏻盐。在类似条件下，N-取代链烷醇胺与 1-酰氨基-2,2-二氯乙烯基-（三苯基）氯化鏻反应生成 1,3-恶唑烷-2-亚基衍生物，其中三苯基鏻基团位于侧链。新合成化合物的结构已通过元素分析、IR、1Н、13С、31Р NMR 光谱、质谱和单晶 X 射线衍射得到可靠证明。图形概要
• Evaluation of Anticancer Activity of 1,3‐Oxazol‐4‐ylphosphonium Salts <i>in Vitro</i>
  作者：Mykhailo Brusnakov、Olexandr Golovchenko、Yevheniia Velihina、Oleksandr Liavynets、Victor Zhirnov、Volodymyr Brovarets

  DOI：10.1002/cmdc.202200319

  日期：2022.10.19

  Excellent anticancer activity of 1,3-oxazol-4-ylphosphonium salts has been demonstrated in a total panel of NCI tumor cell lines. The average values of the antitumor activity parameters of the most potent derivatives ranged from 0.3–1.1 μM (GI50), 1.2–2.5 μM (TGI), and 5–6 μM (LC50). The cytotoxicity vector of the compound 9 showed a high positive correlation with standard antitumor agents that induce

  1,3-恶唑-4-基鏻盐的优异抗癌活性已在所有 NCI 肿瘤细胞系中得到证实。最有效的衍生物的抗肿瘤活性参数的平均值范围为0.3–1.1 μM (GI 50 )、1.2–2.5 μM (TGI) 和5–6 μM (LC 50 )。化合物9的细胞毒性载体与标准抗肿瘤药物呈高度正相关，标准抗肿瘤药物通过半胱天冬酶依赖性内在线粒体途径诱导细胞凋亡。可以推荐最活跃的化合物（ 9、1和4 ）在其基础上进一步深入研究和合成具有抗肿瘤活性的新的更有效的衍生物。
• Kurg, V. V.; Brovarets, V. S.; Drach, B. S., Journal of general chemistry of the USSR, 1991, vol. 61, # 4.1, p. 793 - 797
  作者：Kurg, V. V.、Brovarets, V. S.、Drach, B. S.

  DOI：——

  日期：——
• In silico and in vitro studies of a number PILs as new antibacterials against MDR clinical isolate <i>Acinetobacter baumannii</i>
  作者：Maria M. Trush、Vasyl Kovalishyn、Diana Hodyna、Olexandr V. Golovchenko、Svitlana Chumachenko、Igor V. Tetko、Volodymyr S. Brovarets、Larysa Metelytsia

  DOI：10.1111/cbdd.13678

  日期：2020.6

  AbstractQSAR analysis of a set of previously synthesized phosphonium ionic liquids (PILs) tested against Gram‐negative multidrug‐resistant clinical isolate Acinetobacter baumannii was done using the Online Chemical Modeling Environment (OCHEM). To overcome the problem of overfitting due to descriptor selection, fivefold cross‐validation with variable selection in each step of the model development was applied. The predictive ability of the classification models was tested by cross‐validation, giving balanced accuracies (BA) of 76%–82%. The validation of the models using an external test set proved that the models can be used to predict the activity of newly designed compounds with a reasonable accuracy within the applicability domain (BA = 83%–89%). The models were applied to screen a virtual chemical library with expected activity of compounds against MDR Acinetobacter baumannii. The eighteen most promising compounds were identified, synthesized, and tested. Biological testing of compounds was performed using the disk diffusion method in Mueller‐Hinton agar. All tested molecules demonstrated high anti‐A. baumannii activity and different toxicity levels. The developed classification SAR models are freely available online at http://ochem.eu/article/113921 and could be used by scientists for design of new more effective antibiotics.
• Lobanov, O. P.; Martynyuk, A. P.; Drach, B. S., Journal of general chemistry of the USSR, 1980, vol. 50, p. 1816 - 1824
  作者：Lobanov, O. P.、Martynyuk, A. P.、Drach, B. S.

  DOI：——

  日期：——