3-[(4-Chloro-2-methylphenoxy)methyl]-7-(4-chlorophenyl)-5,6-dihydroimidazo[2,1-c][1,2,4]triazole | 1018855-88-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-[(4-Chloro-2-methylphenoxy)methyl]-7-(4-chlorophenyl)-5,6-dihydroimidazo[2,1-c][1,2,4]triazole
• CAS: 1018855-88-3
• 化学式: C₁₈H₁₆Cl₂N₄O
• 分子量: 375.257
• InChiKey: FIFYEZQKHJFFLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  43.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[(4-Chloro-2-methylphenoxy)methyl]-7-(4-chlorophenyl)-5,6-dihydroimidazo[2,1-c][1,2,4]triazole 生成 氢氰酸 、 二氧化碳 、 4-氯-2-甲基苯酚 、 氨 、 水 、 对氯苯胺 、 乙腈
  参考文献：
  名称：

  二取代稠合 1,2,4-三唑的热性质和分解机理被认为是潜在的抗癌和抗菌剂

  摘要：

  在评估潜在药剂的治疗效用时，耐热性是一个非常重要的参数。因此，使用同时热分析：热重/微分法研究了二取代稠合 1,2,4-三唑（可能是潜在的抗癌和抗菌剂）在氦气和合成空气中的热行为和分解机理。扫描量热法 (TG/DTG/DSC) 与傅里叶变换红外光谱在线耦合。经证实，受试化合物的热稳定性直接取决于它们的结构，因此也取决于氯原子作为取代基的数量。二取代稠合 1,2,4-三唑在惰性条件下的热解过程分为两个主要的、非良好分离的阶段，与 NH 的排放有关3、HCN、乙腈、带OH基的芳烃、带NH 2基的芳烃、H 2 O、CO 2和烯烃碎片。然而，这些化合物在合成空气气氛中的热稳定性与它们在氦气气氛中的热稳定性相当或更低。测试化合物的分解至少经过三个主要阶段，导致释放出与惰性条件下相同类型的挥发物，此外，对于没有或一个氯原子作为取代基的化合物，还会释放出 CO 和一些羰基碎片。结果表明，在惰性条件下加热测试的二取代稠合

  DOI：

  10.1007/s10973-022-11737-2
• 作为产物：
  描述：

  2-甲基-4-氯苯氧乙酸 、 1-(4-chlorophenyl)-2-hydrazinoimidazoline 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以66.4%的产率得到3-[(4-Chloro-2-methylphenoxy)methyl]-7-(4-chlorophenyl)-5,6-dihydroimidazo[2,1-c][1,2,4]triazole
  参考文献：
  名称：

  Synthesis, determination of the lipophilicity, anticancer and antimicrobial properties of some fused 1,2,4-triazole derivatives

  摘要：

  3-Unsubstituted and 3-substituted-7-aryl-5H-6,7-dihydroimidazo[2,1-c][1,2,4]triazoles (1-14) were designed and obtained from biologically active 1-aryl-2-hydrazonoimidazolidines by cyclocondensation reaction with triethyl orthoformates (1-4), phenoxyacetic acid derivatives (5-13) and carbon disulfide (14), respectively. Their chemical structures were confirmed by IR, H-1 NMR, 13 C NMR, MS spectra and elemental analysis. In the high performance liquid chromatographic series of experiments, fourteen synthesized compounds (1-14) were chromatographed on octadecyl silica adsorbent and their lipophilicity parameter (log k(w)) was determined using various aqueous systems: mixture of water and organic modifiers (methanol - MeOH, acetorritrile - MeCN or dioxane - DX). Compounds 7 and 12 were evaluated for their cytotoxic activity against three cancer cell lines: human Caucasian colon adenocarcinoma cell line - LS180 (ECACC 87021202), human uterus carcinoma cell line - SiHa (ECACC 85060701) and human breast carcinoma cell line - T47D (ECACC 85102201). Compound 12 was found to be the most effective in vitro against human colon adenocarcinoma cell line (LS 180). Moreover, the distinctly marked lower cytotoxicity of compounds 7 and 12 against the normal cell line - human skin fibroblasts (HSF) and almost several-fold higher against the examined cancer cell lines was ascertained. The cytotoxic effect of imidazotriazole 7 was noticed on DNA structure of breast cancer cell line (T47D) by using the comet assay. Compound 7 in concentration of 29.3 mu M was found to possess efficiency for DNA strand breakage. In particular, this led to cutting of the DNA strands and formation of small fragments of DNA - two higher and one lighter in comparison with control DNA. Moreover, significant viability decreases in the human leukaemic RPMI 8226 cells treated with different concentrations of imidazotriazoles 8-12 were observed, suggesting their antiproliferative properties. Besides, three tested compounds (9, 13, 14) revealed significant antimicrobial activities with MIC values in the range of 30.9-44.0 mu M. Compound 13 showed superior antibacterial activity to ampicillin and chloramphenicol in vitro, whereas 14 displayed superior antifungal activity to miconazole. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.03.033

文献信息

• Synthesis, determination of the lipophilicity, anticancer and antimicrobial properties of some fused 1,2,4-triazole derivatives
  作者：Krzysztof Sztanke、Tomasz Tuzimski、Jolanta Rzymowska、Kazimierz Pasternak、Martyna Kandefer-Szerszeń

  DOI：10.1016/j.ejmech.2007.03.033

  日期：2008.2

  3-Unsubstituted and 3-substituted-7-aryl-5H-6,7-dihydroimidazo[2,1-c][1,2,4]triazoles (1-14) were designed and obtained from biologically active 1-aryl-2-hydrazonoimidazolidines by cyclocondensation reaction with triethyl orthoformates (1-4), phenoxyacetic acid derivatives (5-13) and carbon disulfide (14), respectively. Their chemical structures were confirmed by IR, H-1 NMR, 13 C NMR, MS spectra and elemental analysis. In the high performance liquid chromatographic series of experiments, fourteen synthesized compounds (1-14) were chromatographed on octadecyl silica adsorbent and their lipophilicity parameter (log k(w)) was determined using various aqueous systems: mixture of water and organic modifiers (methanol - MeOH, acetorritrile - MeCN or dioxane - DX). Compounds 7 and 12 were evaluated for their cytotoxic activity against three cancer cell lines: human Caucasian colon adenocarcinoma cell line - LS180 (ECACC 87021202), human uterus carcinoma cell line - SiHa (ECACC 85060701) and human breast carcinoma cell line - T47D (ECACC 85102201). Compound 12 was found to be the most effective in vitro against human colon adenocarcinoma cell line (LS 180). Moreover, the distinctly marked lower cytotoxicity of compounds 7 and 12 against the normal cell line - human skin fibroblasts (HSF) and almost several-fold higher against the examined cancer cell lines was ascertained. The cytotoxic effect of imidazotriazole 7 was noticed on DNA structure of breast cancer cell line (T47D) by using the comet assay. Compound 7 in concentration of 29.3 mu M was found to possess efficiency for DNA strand breakage. In particular, this led to cutting of the DNA strands and formation of small fragments of DNA - two higher and one lighter in comparison with control DNA. Moreover, significant viability decreases in the human leukaemic RPMI 8226 cells treated with different concentrations of imidazotriazoles 8-12 were observed, suggesting their antiproliferative properties. Besides, three tested compounds (9, 13, 14) revealed significant antimicrobial activities with MIC values in the range of 30.9-44.0 mu M. Compound 13 showed superior antibacterial activity to ampicillin and chloramphenicol in vitro, whereas 14 displayed superior antifungal activity to miconazole. (c) 2007 Elsevier Masson SAS. All rights reserved.
• Thermal properties and decomposition mechanism of disubstituted fused 1,2,4-triazoles considered as potential anticancer and antibacterial agents
  作者：Marta Worzakowska、Małgorzata Sztanke、Krzysztof Sztanke

  DOI：10.1007/s10973-022-11737-2

  日期：2022.12

  Thermal resistance is a very important parameter when assessing the therapeutic usefulness of potential pharmaceutics. Therefore, the thermal behaviour and the decomposition mechanism in the atmosphere of helium and synthetic air of disubstituted fused 1,2,4-triazoles—which may be potential anticancer and antibacterial agents—were studied with a use of simultaneous thermal analysis: thermogravimetry/differential

  在评估潜在药剂的治疗效用时，耐热性是一个非常重要的参数。因此，使用同时热分析：热重/微分法研究了二取代稠合 1,2,4-三唑（可能是潜在的抗癌和抗菌剂）在氦气和合成空气中的热行为和分解机理。扫描量热法 (TG/DTG/DSC) 与傅里叶变换红外光谱在线耦合。经证实，受试化合物的热稳定性直接取决于它们的结构，因此也取决于氯原子作为取代基的数量。二取代稠合 1,2,4-三唑在惰性条件下的热解过程分为两个主要的、非良好分离的阶段，与 NH 的排放有关3、HCN、乙腈、带OH基的芳烃、带NH 2基的芳烃、H 2 O、CO 2和烯烃碎片。然而，这些化合物在合成空气气氛中的热稳定性与它们在氦气气氛中的热稳定性相当或更低。测试化合物的分解至少经过三个主要阶段，导致释放出与惰性条件下相同类型的挥发物，此外，对于没有或一个氯原子作为取代基的化合物，还会释放出 CO 和一些羰基碎片。结果表明，在惰性条件下加热测试的二取代稠合