4-氨基-3-甲基-1H-1,2,4-噻唑-5(4H)-酮 | 4194-37-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-氨基-3-甲基-1H-1,2,4-噻唑-5(4H)-酮
• 英文名称: 4-amino-3-methyl-1H-1,2,4-triazol-5(4H)-one
• 英文别名: 4-amino-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one；3-methyl-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-one；4-amino-3-methyl-1,2,4-triazol-5(4H)-one；4-amino-3-methyl-1H-1,2,4-triazol-5-one
• CAS: 4194-37-0
• 化学式: C₃H₆N₄O
• 分子量: 114.107
• InChiKey: RSHSEEWONPESSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  70.7
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  4-氨基-3-甲基-1H-1,2,4-噻唑-5(4H)-酮 生成 4-amino-5-methyl-2-(tertbutylaminocarbonyl)-1,2,4-triazolin-3-one
  参考文献：
  名称：

  LINDIG, MARKUS;FINDELSEN, KURT;MULLER, KLAUS-HELMUT;SANTEL, HANS-JOACHIM;+

  摘要：

  DOI：
• 作为产物：
  描述：

  (1-乙氧基乙基亚基)肼基甲酸乙酯 在 肼 作用下， 生成 4-氨基-3-甲基-1H-1,2,4-噻唑-5(4H)-酮
  参考文献：
  名称：

  一些新型4,5-二氢-1H-1,2,4-三唑-5-酮衍生物的合成及其对乙酰胆碱酯酶的抑制作用；一项体外和计算机模拟研究

  摘要：

  摘要 本研究通过 3-alkyl(aryl)-4-amino-4,5-dihydro-1 H的缩合反应合成了一系列含有 1,2,4-三唑结构的新型席夫碱 (4a-4h) -1,2,4-三唑-5-酮与 3-(4-甲基苯磺酰氧基)-苯甲醛。3-alkyl(aryl)-4-[3-(4-methylsulfonyloxy)-benzylidenamino]-4,5-dihydro-1 H -1,2,4-triazol-5-ones (4a-h) 的结构是通过一系列光谱技术（FT-IR、1 H NMR、13 C NMR 和元素分析）确定。此外，还确定了新合成的席夫碱对乙酰胆碱酯酶 (AChE) 的酶抑制特性。它们的 K i值计算在 0.70 ± 0.07–8.65 ± 5.6 µM 的范围内。此外，他们的IC在 0.43–3.87 µM 的范围内计算了50 个值。最后，使用 Chimera 和 AutoDock

  DOI：

  10.1080/07391102.2022.2066021

文献信息

• Herbicidal substituted 4-sulphonylamino-2-azinyl-1,2,4-triazol-3-ones
  申请人：Bayer Aktiengesellschaft

  公开号：US04988381A1

  公开（公告）日：1991-01-29

  Herbicidal substituted sulphonylaminotriazolinones of the formula ##STR1## in which R.sup.1 represents an optionally substituted radical from the group consisting of alkyl, aralkyl, aryl and heteroaryl, R.sup.2 represents hydrogen or the group --SO.sub.2 --R.sup.1 where R.sup.1 has the abovementioned meaning, R.sup.3 represents hydrogen, halogen, hydroxyl, mercapto, amino or an optionally substituted radical from the group consisting of alkyl, cycloalkyl, aralkyl, aryl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkenylthio, alkinylthio, aralkoxy, aralkylthio, alkylamino and dialkylamino, R.sup.4 represents hydrogen, halogen, hydroxyl, amino or an optionally substituted radical from the group consisting of alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino and dialkylamino, X represents nitrogen or a CH group, Y represents nitrogen or a CR.sup.5 group where R.sup.5 represents hydrogen, halogen, cyano, alkyl, formyl, alkylcarbonyl or alkoxycarbonyl, and Z represents nitrogen or a CR.sup.6 group where R.sup.6 represents hydrogen, halogen, hydroxyl, amino or an optionally substituted radical from the group consisting of alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino and dialkylamino, and salts thereof. Intermediates of the formulas ##STR2## are also new.

  Herbicidal substituted sulphonylaminotriazolinones的化学式为##STR1##，其中R.sup.1代表从烷基、芳基、芳基烷基和杂环芳基组成的可选择取代基团，R.sup.2代表氢或--SO.sub.2--R.sup.1基团，其中R.sup.1具有上述含义，R.sup.3代表氢、卤素、羟基、巯基、氨基或从烷基、环烷基、芳基、烷氧基、烯氧基、炔氧基、烷硫基、烷砜基、烷磺基、烯硫基、炔硫基、芳基氧基、芳基硫基、烷基氨基和二烷基氨基组成的可选择取代基团，R.sup.4代表氢、卤素、羟基、氨基或从烷基、烷氧基、烷硫基、烷砜基、烷磺基、烷基氨基和二烷基氨基组成的可选择取代基团，X代表氮或CH基团，Y代表氮或CR.sup.5基团，其中R.sup.5代表氢、卤素、氰基、烷基、甲酰基、烷基羰基或烷氧羰基，Z代表氮或CR.sup.6基团，其中R.sup.6代表氢、卤素、羟基、氨基或从烷基、烷氧基、烷硫基、烷砜基、烷磺基、烷基氨基和二烷基氨基组成的可选择取代基团，以及其盐。化合物##STR2##的中间体也是新的。
• Synthesis of new derivatives of 4-amino-2,4-dihydro-1,2,4-triazol-3-one as potential antibacterial agents
  作者：Frédérique Malbec、René Milcent、Patrick Vicart、Anne Marie Bure

  DOI：10.1002/jhet.5570210641

  日期：1984.11

  characterised by their sharp melting points, elemental analysis, ir and 1H nmr spectra. These new derivatives of 5-nitro-2-furaldehyde were screened for their antibacterial activities. Most of the compounds showed good activity against one test organism, Staphylococcus aureus. For a few compounds, C.M.I. ranged from 4 to 8 μg/ml (higher results than nitrofurantoin).

  三十个新的2-取代的-4-氨基-5-烷基或芳基-2,4-二氢-1,2,4-三唑-3-酮和十个2-取代的-5-烷基或芳基-4-（5-合成了硝基-2-糠基亚氨基）氨基-2,4-二氢-1,2,4-三唑-3-酮，并通过其尖锐的熔点，元素分析，ir和1 H nmr光谱对其进行了表征。筛选了5-硝基-2-呋喃甲醛的这些新衍生物的抗菌活性。大多数化合物对一种测试生物金黄色葡萄球菌显示出良好的活性。对于一些化合物，CMI范围为4至8μg/ ml（比呋喃妥因更高的结果）。
• Preparation and antimicrobial activity evaluation of some new bi- and triheterocyclic azoles
  作者：Serpil Demirci、Serap Basoglu、Arif Bozdereci、Neslihan Demirbas

  DOI：10.1007/s00044-013-0498-3

  日期：2013.10

  synthesized compounds were screened for their antimicrobial activities. In general, most compounds except 22 were Found (%) to be active against Mycobacterium smegmatis, Candida albicans and/or Saccharomyces cerevisiae. Furthermore, 9a and b, which are Mannich bases incorporating morpholine or piperazine nucleus, exhibited excellent antimicrobial activity on test microorganisms. In addition, the hydrazide

  所述carbothioamides合成（5，13，22）进行从3开始ħ -1,2,4-三唑-3-酮（2，17）由几个步骤，然后，这些carbothioamides转化为包含1三杂环化合物1,2,4-三唑，咪唑和1,3-噻唑（idinone）部分。化合物2与3，4-二氟硝基苯的反应得到2-（2-氟-4-硝基苯基）衍生物10。通过硝基的还原，将化合物10转化为亚芳基氨基衍生物（12a，b）。另一方面，酰肼的处理（20）是从17开始获得的，与几种芳族醛生成相应的芳基酰肼（21a – c）。化合物2与合适的杂环胺之间的曼尼希反应导致2的N-烷基化。筛选所有新合成的化合物的抗菌活性。通常，发现除22种化合物外，大多数化合物（％）对耻垢分枝杆菌，白色念珠菌和/或酿酒酵母具有活性。此外，9a和b，是结合了吗啉或哌嗪核的曼尼希碱，对测试微生物表现出出色的抗菌活性。此外，发现酰肼4（％）对Ec和Yp具有活性。
• 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。
• Reduction, Mannich reaction and antimicrobial activity evaluation of some new 1,2,4-triazol-3-one derivatives
  作者：SEDA FANDAKLI、SERAP BAŞOĞLU、HAKAN BEKTAŞ、MELTEM YOLAL、AHMET DEMİRBAŞ、ŞENGÜL ALPAY KARAOĞLU

  DOI：10.3906/kim-1103-23

  日期：——

  Ethyl[4-arylmethyleneamino-3-(4-metylphenyl)-5-oxo-4,5-dihydro- 1H-1,2,4-triazole-1-yl]acetates (3a-e and 10a-d) were obtained starting from 4-amino-2,4-dihydro-3H-1,2,4-triazol-3-ones (1 and 9) in 2 steps. The treatment of 3a-e with NaBH_4 resulted in the formation of 3 kinds of product incorporating carboxcilic acid (4a-c) or alcohol (5a-e) functionality. [4-[(4-Methoxyphenyl)methylene]amino}- and 4-[pyridin-4-ylmethylene]amino}-3-(4-methylphenyl)-5-oxo-4,5-dihydro-1H- 1,2,4-triazole-1-yl] acetic acids (6a, 6e) were obtained by the hydrolysis of the corresponding esters (5a-5e). The treatment of 6a with NaBH_4 caused the reduction of only the imine bond; the carboxyl group remained unchanged. Then this carboxylic acid was converted to the corresponding hydrazide (8) in 2 steps by reaction with ethanol and hydrazine hydrate, respectively. The synthesis of Mannich bases was performed by the reaction of the corresponding 1,2,4-triazoles containing an imine group (10a-d) with several primary or secondary amines including morpholine or piperazine nucleus. All newly synthesized compounds were screened for their antimicrobial activity. The antimicrobial activity study revealed that the Mannich bases (11-16) showed good activity against the test microorganisms as compared with ampicillin.

  通过两步法，从4-氨基-2,4-二氢-3H-1,2,4-三唑-3-酮（1和9）出发，得到乙基[4-芳基亚甲基氨基-3-(4-甲基苯)-5-氧-4,5-二氢-1H-1,2,4-三唑-1-基]乙酸酯（3a-e和10a-d）。将3a-e与NaBH₄处理后，形成了三种包含羧酸（4a-c）或醇（5a-e）官能团的产物。通过水解相应的酯（5a-5e）得到了[4-[(4-甲氧基苯)亚甲基]氨基}-和4-[吡啶-4-基亚甲基]氨基}-3-(4-甲基苯)-5-氧-4,5-二氢-1H-1,2,4-三唑-1-基]乙酸（6a, 6e）。将6a与NaBH₄处理导致仅亚胺键的还原；羧基保持不变。然后，通过与乙醇和水合肼的反应，这种羧酸在两步反应中转化为相应的肼（8）。Mannich碱的合成是通过将含有亚胺基团的相应1,2,4-三唑（10a-d）与几种一、二级胺（包括哌啶或摩尔啶）反应进行的。所有新合成的化合物均进行了抗微生物活性的筛选。抗微生物活性研究表明，Mannich碱（11-16）与青霉素相比，对测试微生物显示出良好的活性。