4,4'-bis(3-methyl-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl)diphenylmethane | 1130206-85-7

• 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: 4,4'-bis(3-methyl-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl)diphenylmethane
• 英文别名: 4,4'-(methylenedi-4,1-phenylene)bis(2,4-dihydro-5-methyl-3H-1,2,4-triazol-3-one)；4,4'-bis(3-methyl-1,2,4-triazolin-5-on-4-yl)diphenylmethane；4,4'-(Methylenedi-4,1-phenylene)bis(2,4-dihydro-5-methyl-3h-1,2,4-triazol-3-one)；3-methyl-4-[4-[[4-(3-methyl-5-oxo-1H-1,2,4-triazol-4-yl)phenyl]methyl]phenyl]-1H-1,2,4-triazol-5-one
• CAS: 1130206-85-7
• 化学式: C₁₉H₁₈N₆O₂
• 分子量: 362.391
• InChiKey: AUHKMDUPHDEWQN-UHFFFAOYSA-N

物化性质

• 熔点：
  307-309 °C
• 密度：
  1.40±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  89.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4,4'-二苯甲烷二异氰酸酯、2,4'-二苯甲烷二异氰酸酯和2,2'-二苯甲烷二异氰酸酯的混合物 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 39.0h， 生成 4,4'-bis(3-methyl-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl)diphenylmethane
  参考文献：
  名称：

  某些氨基脲，1,2,4-三唑酮和吡唑啉酮衍生物的抗氧化评价

  摘要：

  合成具有杂环1-14的1,2,4-三唑，吡唑和氨基脲为具有有趣药理学特征的化合物。所有的人都进行了体外抗氧化活性研究。一些化合物在上述测定中显示出显著作用。最有希望的是一组吡唑啉酮。 该作用主要取决于酰胺基上的取代基。发现化合物8和10显示出与广泛使用的参比抗氧化剂6-羟基-2,5,7,8-四甲基苯并-2-羧酸（Trolox）相当的最高抗氧化剂容量。

  DOI：

  10.2174/157018011797655188

文献信息

• Synthesis, experimental and theoretical investigations of some new 4,4′-bis(3-substituted-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl)diphenylmethane derivatives
  作者：Monika Pitucha、Piotr Borowski、Zbigniew Karczmarzyk、Andrzej Fruziński

  DOI：10.1016/j.molstruc.2008.09.002

  日期：2009.2

  5-dihydro-1H-1,2,4-triazol-5-one-4-yl)diphenylmethane derivatives 3 were synthesized in the cyclization reaction of semicarbazide derivatives 2 in alkaline solution. The synthesized compounds were characterized by elemental analyses, IR, 1H and 13C NMR, as well as MS. Molecular structure of compound 3a was determined by the X-ray analysis. Theoretical calculations (DFT/B3LYP/6-311G∗∗) of molecular structures

  摘要 通过氨基脲衍生物2的环化反应合成了4,4'-双(3-取代-4,5-二氢-1H-1,2,4-三唑-5-酮-4-基)二苯甲烷衍生物3。在碱性溶液中。合成的化合物通过元素分析、IR、1H 和 13C NMR 以及 MS 进行表征。化合物3a的分子结构由X射线分析确定。对所有最终（环状）化合物进行了分子结构的理论计算（DFT/B3LYP/6-311G**）。此外，通过单参数和 SQM 缩放方法再现了 3a 的振动谱，并提出了频带分配。研究的新化合物表现出镇痛特性。
• Anticancer Screening and Structure Activity Relationship Study of Some Semicarbazides and 1,2,4-Triazolin-5-ones
  作者：Monika Pitucha、Jolanta Rzymowska

  DOI：10.2174/157018012800673047

  日期：2012.5.1

  In this paper some semicarbazide and 1,2,4-triazolin-5-one derivatives are evaluated in vitro for their anticancer activity towards human tumour cell line: ovary (TOV 112D), lung (A 549), breast (T47D) and uterus (Hela). Compounds 2-4 have been found to show the most effective in vitro activity against ovary cancer cell line. For compound 4 the growth inhibition (80% and 70%) is observed in two concentrations (100 μg/ml and 50 μg/ml). The cytotoxic effect of examined compounds seems to be dose-dependent and time-dependent. Compound 7 has GI=80% values towards the breast cancer cell line in concentration of 100 μg/ml. Structure-activity relationship (SAR) studies are carried out for all the compounds of the series. Compounds 2-4 show an activity profile that can be improved through medicinal chemistry strategies.

  本文评估了一些半咔嗪和 1,2,4-三唑啉-5-酮衍生物对人类肿瘤细胞株（卵巢（TOV 112D）、肺（A 549）、乳腺（T47D）和子宫（Hela））的体外抗癌活性。研究发现，化合物 2-4 对卵巢癌细胞株具有最有效的体外活性。在两种浓度（100 微克/毫升和 50 微克/毫升）下，化合物 4 的生长抑制率分别为 80% 和 70%。所研究化合物的细胞毒性作用似乎是剂量依赖性和时间依赖性的。浓度为 100 μg/ml 的化合物 7 对乳腺癌细胞株的 GI 值为 80%。对该系列的所有化合物都进行了结构-活性关系（SAR）研究。化合物 2-4 显示出了可通过药物化学策略加以改进的活性特征。
• Synthesis and antinociceptive activity of 4,4′-bis(1-substituted-semicarbazidyl)diphenylmethane and 4,4′-bis(5-substituted-2,4-dihydro-3-oxo-3H-1,2,4-triazol-4-yl)diphenylmethane derivatives
  作者：Monika Pitucha、Anna Chodkowska、Mariusz Maciejewski、Ewa Jagiello-Wójtowicz、Anna Pachuta-Stec

  DOI：10.1007/s00706-009-0242-3

  日期：2010.2

  In the reaction of 4,4'-diphenylmethane diisocyanate with carboxylic acid hydrazides, 4,4'-bis(1-substituted-semicarbazidyl) diphenylmethane derivatives were obtained. Depending on their chemical nature, cyclization of these compounds in alkaline medium led to the formation of two groups of compounds: bis(2,4-dihydro-3H-1,2,4-triazol-3-one) derivatives or carboxylic acids. The pharmacological effects of the selected compounds on the central nervous system in mice were investigated. Strong antinociceptive properties of some derivatives, at a wide range of doses, were observed.
• Synthesis and RP HPLC studies of biologically active semicarbazides and their cyclic analogues 1,2,4-triazol-3-ones
  作者：Monika Pitucha、Joanna Matysiak、Bogdan Senczyna

  DOI：10.1007/s00706-011-0715-z

  日期：2012.4

  The retention behaviour of semicarbazides and their cyclic analogues 1,2,4-triazol-3-ones, has been investigated by RP-8, RP-18 and IAM HPLC. The structures of new derivatives were proved by elemental analyses, IR, H-1 NMR and C-13 NMR spectroscopy. The compounds showed regular retention behaviour in three chromatographic systems; their log k values decreased linearly with the increasing concentration of an organic modifier in the mobile phase. The ratio of the intercept (log k (w)) to the slope of compounds is constant and the same for both groups of compounds on C18 and IAM stationary phases. Differences between log k (w) values from the octadecyl stationary phase of corresponding cyclic and linear derivatives are constant, and they are related to the mechanism of synthesis of 1,2,4-triazol-3-ones from linear substrate semicarbazides, which was confirmed by modelling studies. Good correlations between log k (w) parameters obtained by RP-8 or RP-18 and determined by the computational approach log P were found.