2-(4-amino-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)acetohydrazide | 778591-72-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4-amino-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)acetohydrazide
• 英文别名: 2-(4-Amino-3-methyl-5-oxo-4,5-dihydro-1 h-1,2,4-triazol-1-yl)acetohydrazide；2-(4-amino-3-methyl-5-oxo-1,2,4-triazol-1-yl)acetohydrazide
• CAS: 778591-72-3
• 化学式: C₅H₁₀N₆O₂
• 分子量: 186.173
• InChiKey: CUPDCOZGLLBLMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  117
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(4-amino-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)acetohydrazide 以 乙醇 为溶剂， 反应 4.0h， 生成 4-Amino-5-methyl-2-(4-phenyl-5-thioxo-4,5-dihydro-1H-[1,2,4]triazol-3-ylmethyl)-2,4-dihydro-[1,2,4]triazol-3-one
  参考文献：
  名称：

  Synthesis and antimicrobial activities of some new 1-(5-phenylamino-[1,3,4]thiadiazol-2-yl)methyl-5-oxo-[1,2,4]triazole and 1-(4-phenyl-5-thioxo-[1,2,4]triazol-3-yl)methyl-5-oxo- [1,2,4]triazole derivatives

  摘要：

  Acetic acid ethyl esters containing 5-oxo-[1,2,4]triazole ring (2) were synthesized by the condensation of compounds 1a-f with ethyl bromoacetate in basic media. The reaction of compounds 2a-f with hydrazine hydrate led to the formation of acid hydrazides (3a-f). The treatment of compounds 3 with two divers aromatic aldehydes resulted in the formation of arylidene hydrazides as cis-tralls conformers (4a,c,e,f, 5a,e,f). The thiosemicarbazide derivatives (6a,c,d,f) were afforded by the reaction of corresponding compounds 3 with phenylisothiocyanate. The treatment of compounds 6a,c,d,f with sulfuric acidic caused the conversion of side-chain of compounds 6a,c,d,f into 1,3,4-thiadiazol ring; thus, compounds 7a,c,d,f were obtained. On the other hand, the cyclization of compounds 6a,c,d,f in the presence of 2 N NaOH resulted in the formation of compounds 8a,c,d,f containing two [1,2,4]triazole rings which are linked to each other via it methylene bridge. Compounds 4a, f, 5a, 7a, d, f, 8a and d have shown antimicrobial activity against one or more microorganism, but no antifungal activity has been observed against yeast like fungi. Also inhibitory effect on mycelial growth by compounds 4e, 7d and 8f hits been observed. Compounds 4c and 5f were found to possess antitumor active towards breast cancer. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.06.007
• 作为产物：
  描述：

  ethyl (4-amino-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)acetate 在 一水合肼 作用下， 以 正丁醇 为溶剂， 生成 2-(4-amino-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)acetohydrazide
  参考文献：
  名称：

  香豆素-三唑杂化分子作为潜在抗肿瘤剂和胰脂肪酶剂的设计、合成和生物学评价

  摘要：

  报道了一些香豆素-三唑杂化分子的抗肿瘤和抗脂肪酶活性的设计、合成和研究。这些杂化分子的合成是在微波辐射和常规加热程序下进行的。研究了新合成的杂交分子作为四种肿瘤细胞系（BT20 人乳腺癌、SK-Mel 128 黑色素瘤、DU-145 前列腺癌和 A549 肺癌）和猪胰脂肪酶 (PPL) 的抑制剂。这些化合物中的大多数对所测试的肿瘤细胞系显示出显着的抗肿瘤活性，化合物 8i 和 8l 在 10 μM 的浓度下显示出最佳的抗脂肪酶活性，分别为 99.30 ± 0.56% 和 99.85 ± 1.21%。

  DOI：

  10.1002/ardp.201600369

文献信息

• Microwave-assisted synthesis of some new coumarin derivatives including 1,2,4-triazol-3-one and investigation of their biological activities
  作者：Bahittin Kahveci、Fatih Yılmaz、Emre Menteşe、Serdar Ülker

  DOI：10.1007/s10593-015-1714-5

  日期：2015.5

  By using the microwave technology, a new protocol has been developed for the synthesis of new coumarin derivatives including 1,2,4-triazol-3-one skeleton. This protocol proves to be efficient and environmentally friendly in terms of easy work-up and good yields. All newly synthesized compounds were screened for their antimicrobial activity and lipase inhibition. Most of the compounds were found to

  通过使用微波技术，已经开发了用于合成包括1,2,4-三唑-3-酮骨架的新香豆素衍生物的新方案。从易于处理和高产量的角度来看，该协议被证明是高效且对环境友好的。筛选所有新合成的化合物的抗菌活性和脂肪酶抑制作用。发现大多数化合物对大肠杆菌有效。N '-[4-氨基-3-（2-溴苄基）-5-氧代-4,5-二氢-1 H -1,2,4-三唑-1-基]乙酰基} -6-溴-2 -oxo-2 H色烯-3-碳酰肼和N '-[4-氨基-3-（3,4-二氯苄基）-5-oxo-4,5-二氢-1 H -1,2,4-三唑-1-基]乙酰基} -6-溴-2-氧代-2 H-色烯-3-碳酰肼对脂肪酶的抑制作用良好。
• Design, Synthesis, and Biological Evaluation of Coumarin-Triazole Hybrid Molecules as Potential Antitumor and Pancreatic Lipase Agents
  作者：Bahittin Kahveci、Fatih Yılmaz、Emre Menteşe、Serdar Ülker

  DOI：10.1002/ardp.201600369

  日期：2017.8

  The design, synthesis, and investigation of antitumor and anti‐lipase activities of some coumarin–triazole hybrid molecules are reported. The synthesis of these hybrid molecules was performed under microwave irradiation and conventional heating procedures. The newly synthesized hybrid molecules were investigated as inhibitors against four tumor cell lines (BT20 human breast carcinoma, SK‐Mel 128 melanoma

  报道了一些香豆素-三唑杂化分子的抗肿瘤和抗脂肪酶活性的设计、合成和研究。这些杂化分子的合成是在微波辐射和常规加热程序下进行的。研究了新合成的杂交分子作为四种肿瘤细胞系（BT20 人乳腺癌、SK-Mel 128 黑色素瘤、DU-145 前列腺癌和 A549 肺癌）和猪胰脂肪酶 (PPL) 的抑制剂。这些化合物中的大多数对所测试的肿瘤细胞系显示出显着的抗肿瘤活性，化合物 8i 和 8l 在 10 μM 的浓度下显示出最佳的抗脂肪酶活性，分别为 99.30 ± 0.56% 和 99.85 ± 1.21%。
• Synthesis and antimicrobial activities of some new 1-(5-phenylamino-[1,3,4]thiadiazol-2-yl)methyl-5-oxo-[1,2,4]triazole and 1-(4-phenyl-5-thioxo-[1,2,4]triazol-3-yl)methyl-5-oxo- [1,2,4]triazole derivatives
  作者：Neslihan Demirbas、Sengül Alpay Karaoglu、Ahmet Demirbas、Kemal Sancak

  DOI：10.1016/j.ejmech.2004.06.007

  日期：2004.9

  Acetic acid ethyl esters containing 5-oxo-[1,2,4]triazole ring (2) were synthesized by the condensation of compounds 1a-f with ethyl bromoacetate in basic media. The reaction of compounds 2a-f with hydrazine hydrate led to the formation of acid hydrazides (3a-f). The treatment of compounds 3 with two divers aromatic aldehydes resulted in the formation of arylidene hydrazides as cis-tralls conformers (4a,c,e,f, 5a,e,f). The thiosemicarbazide derivatives (6a,c,d,f) were afforded by the reaction of corresponding compounds 3 with phenylisothiocyanate. The treatment of compounds 6a,c,d,f with sulfuric acidic caused the conversion of side-chain of compounds 6a,c,d,f into 1,3,4-thiadiazol ring; thus, compounds 7a,c,d,f were obtained. On the other hand, the cyclization of compounds 6a,c,d,f in the presence of 2 N NaOH resulted in the formation of compounds 8a,c,d,f containing two [1,2,4]triazole rings which are linked to each other via it methylene bridge. Compounds 4a, f, 5a, 7a, d, f, 8a and d have shown antimicrobial activity against one or more microorganism, but no antifungal activity has been observed against yeast like fungi. Also inhibitory effect on mycelial growth by compounds 4e, 7d and 8f hits been observed. Compounds 4c and 5f were found to possess antitumor active towards breast cancer. (C) 2004 Elsevier SAS. All rights reserved.