1-methyl-5-thioxo-1,2,4-triazolidin-3-one | 22244-62-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-methyl-5-thioxo-1,2,4-triazolidin-3-one
• 英文别名: 1-Methyl-5-thioxo-1,2,4-triazolidinon-(3)；1-Methyl-3-oxo-5-thio-triazolidin-1,2,4；5-mercapto-1-methyl-1,2-dihydro-3H-1,2,4-triazol-3-one；1-methyl-5-sulfanylidene-1,2,4-triazolidin-3-one
• CAS: 22244-62-8
• 化学式: C₃H₅N₃OS
• mdl: MFCD09286598
• 分子量: 131.158
• InChiKey: OOTVRBPTSHCZJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  76.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-methyl-5-thioxo-1,2,4-triazolidin-3-one 在 potassium hydrogen bifluoride 、 氯 作用下， 以 甲醇 、 水 为溶剂， 以41%的产率得到2-Methyl-5-oxo-2,5-dihydro-1H-[1,2,4]triazole-3-sulfonyl fluoride
  参考文献：
  名称：

  Synthesis and Anti-Acetylcholinesterase Activity of Some 5-Substituted 1-Methyl-1H-1,2,4-triazol-3-yl Methanesulfonates

  摘要：

  5-Chloro-1-methyl-1,2-dihydro-3H-1,2,4-triazol-3-one (12) 和 N-isopropyl-2-methyl-5-oxo-2,5-dihydro-1H1,2,4triazole3-sulfonamide (14)。 (14) 由 1-甲基-5-硫酮-1,2,4-三唑啉-3-酮 (7) 制备，并将其转化为甲磺酰胺。 转化为甲磺酸酯 (15) 和 (16)。抗乙酰胆碱酯酶和 (15)和(16)的抗乙酰胆碱酯酶和杀虫活性。 与已知的 5-isobutylthio-1-methyl-1H-1,2,4-triazol-3-yl 甲磺酸盐 (4)。

  DOI：

  10.1071/c96163
• 作为产物：
  描述：

  异硫氰酰甲酸乙酯 、 甲基肼 在 盐酸 作用下， 生成 1-methyl-5-thioxo-1,2,4-triazolidin-3-one
  参考文献：
  名称：

  Synthesis and Anti-Acetylcholinesterase Activity of Some 5-Substituted 1-Methyl-1H-1,2,4-triazol-3-yl Methanesulfonates

  摘要：

  5-Chloro-1-methyl-1,2-dihydro-3H-1,2,4-triazol-3-one (12) 和 N-isopropyl-2-methyl-5-oxo-2,5-dihydro-1H1,2,4triazole3-sulfonamide (14)。 (14) 由 1-甲基-5-硫酮-1,2,4-三唑啉-3-酮 (7) 制备，并将其转化为甲磺酰胺。 转化为甲磺酸酯 (15) 和 (16)。抗乙酰胆碱酯酶和 (15)和(16)的抗乙酰胆碱酯酶和杀虫活性。 与已知的 5-isobutylthio-1-methyl-1H-1,2,4-triazol-3-yl 甲磺酸盐 (4)。

  DOI：

  10.1071/c96163

文献信息

• 1,2,4-Triazolyl-phosphoric and -phosphonic acid esters
  申请人：Ciba-Geigy Corporation

  公开号：US03992399A1

  公开（公告）日：1976-11-16

  1,2,4-Triazolylphosphoric and 1,2,4-triazolylphosphonic acid esters of the formula ##SPC1## Wherein R.sub.1 represents hydrogen, alkyl, cycloalkyl, phenyl, benzyl, or phenethyl, R.sub.2 represents substituted phenyl, benzyl, phenethyl, or unsubstituted diphenylmethyl, .beta.-naphthyl, or ##SPC2## R.sub.3 represents alkyl, alkoxy, alkylthio, amino, monoalkylamino or dialkylamino, R.sub.4 represents alkyl, and X represents oxygen or sulphur, a process for their manufacture and their use in pest control.

  1,2,4-三唑磷酸和1,2,4-三唑磷酸酯的化学式如下：其中R.sub.1代表氢、烷基、环烷基、苯基、苄基或苄苯基，R.sub.2代表取代苯基、苄基、苄乙基或未取代的二苯甲基、β-萘基或R.sub.3的取代基，R.sub.3代表烷基、烷氧基、烷硫基、氨基、单烷基氨基或二烷基氨基，R.sub.4代表烷基，X代表氧或硫。它们的制备方法以及在害虫控制中的用途。
• 1,3-thiazoles and their use as immunomodulators
  申请人：Hoechst Aktiengesellschaft

  公开号：US04762848A1

  公开（公告）日：1988-08-09

  Heterocyclic sulfides of the general formula heterocycle-S-R, a process for their preparation and, in particular, their use for immunostimulation, immunorestoration and cytostatic treatment, and pharmaceutical agents, which contain a sulfide of this type, for these indications.

  本发明涉及一般式为杂环-S-R的杂环硫化物的制备方法，特别是它们用于免疫刺激、免疫恢复和细胞毒素治疗的用途，以及含有此类硫化物的药物制剂，用于上述适应症。
• Process for preparing 1,2,4-triazole derivatives
  申请人：Ciba-Geigy Corporation

  公开号：US04123437A1

  公开（公告）日：1978-10-31

  1,2,4-TRIAZOLE DERIVATIVES WHICH HAVE PARTICULAR IMPORTANCE AS INTERMEDIATES FOR, E.G., THE PREPARATION OF ACTIVE SUBSTANCES FOR PEST CONTROL, CORRESPONDING TO THE FORMULA ##STR1## wherein R.sup.1 represents an unsubstituted or substituted alkyl, alkenyl, or alkynyl, naphthyl, benzyl, phenylethyl, ##STR2## or phenylpropyl radical, or a mono or polycyclic cycloalkyl radical which can be bound by way of an alkylene bridge member, or a substituted phenyl radical, And new processes for the preparation of compounds of the formula ##STR3## wherein R represents hydrogen, an optionally substituted alkyl, alkenyl or alkynyl radical, an optionally substituted phenyl, naphthyl, benzyl, phenylethyl or phenylpropyl radical, a mono- or polycyclic cycloalkyl radical which can be bound by way of an alkylene bridge member and/or be substituted by alkyl, or a partially hydrogenated naphthyl radical, which processes are performed by addition to a hydrazine of the formula R -- NH--NH.sub.2 or to a hydrazone of the formula ##STR4## wherein R has the above given meaning, R.sub.1 represents hydrogen or lower alkyl and R.sub.2 represents lower alkyl, of an alkoxy-carbonyl-isothiocyanate of the formula alkyl--O--CO--NCS and subsequent closure of the triazole ring in the resulting thiosemicarbazide of the formula ##STR5## by the splitting-off of an alkanol (alkyl--OH), are disclosed.

  具有特殊重要性的1,2,4-三唑衍生物，例如，用于制备杀虫剂活性成分的中间体，对应于以下式子：##STR1## 其中R.sup.1表示未取代或取代的烷基，烯基或炔基，萘基，苯甲基，苯乙基， ##STR2## 或苯基丙基基团，或可以通过烷基桥连成员结合的单环或多环环烷基基团，或取代苯基基团。还公开了制备以下式子化合物的新方法：##STR3## 其中R表示氢，可选择取代的烷基，烯基或炔基基团，可选择取代的苯基，萘基，苯甲基，苯乙基或苯基丙基基团，可以通过烷基桥连成员结合并/或被烷基取代的单环或多环环烷基基团以及部分氢化的萘基基团，这些方法通过向式为R-NH-NH.sub.2的肼或式为##STR4## 的肼酮中加入式为烷基-O-CO-NCS的烷氧卡巴酰异硫氰酸酯，并通过裂解烷醇（烷基-OH）闭合所得的硫半脲酸盐的三唑环。
• 1,2,4-Triazolyl-phosphoric acid and phosphonic acid esters
  申请人：Ciba-Geigy Corporation

  公开号：US04054575A1

  公开（公告）日：1977-10-18

  1,2,4-triazolylphosphoric and 1,2,4-triazolylphosphonic acid esters of the formula ##STR1## wherein R.sub.1 represents hydrogen, alkyl, cycloalkyl, phenyl, benzyl, or phenethyl, R.sub.2 represents alkenyl or alkinyl, R.sub.3 represents alkyl, alkoxy, alkylthio, amino, monoalkylamino or dialkylamino, R.sub.4 represents alkyl, and X represents oxygen or sulphur, a process for their manufacture and their use in pest control.

  1,2,4-三唑基磷酸和1,2,4-三唑基膦酸酯的化学式为##STR1##其中R.sub.1代表氢、烷基、环烷基、苯基、苄基或苯乙基，R.sub.2代表烯基或炔基，R.sub.3代表烷基、烷氧基、烷硫基、氨基、单烷基氨基或双烷基氨基，R.sub.4代表烷基，X代表氧或硫。该发明涉及一种制备方法以及在害虫控制中的应用。
• Synthesis and biological evaluation of 2-(Tetrazol-5-yl)sulfonylacetamides as inhibitors of Mycobacterium tuberculosis and Mycobacterium marinum
  作者：Robin Henches、Théo Ozga、Yamin Gao、Zhengchao Tu、Tianyu Zhang、Craig L. Francis

  DOI：10.1016/j.bmcl.2023.129391

  日期：2023.8

  A series of 2-(tetrazol-5-yl)sulfonylacetamide derivatives were synthesized and evaluated for their in vitro inhibitory activity against Mycobacterium tuberculosis (Mtb) and Mycobacterium marinum (Mm). The most active compounds exhibited in vitro MIC90 values of 1.25 μg/mL against Mtb, but they were less effective against Mm (MIC90 ≥ 10 μg/mL). Despite the most active compounds having favourable physicochemical

  合成了一系列2-(四唑-5-基)磺酰基乙酰胺衍生物，并评估了其对结核分枝杆菌(Mtb)和海分枝杆菌(Mm)的体外抑制活性。最活跃的化合物对 Mtb 的体外MIC 90值为 1.25 μg/mL，但对 Mm 的效果较差（MIC 90  ≥ 10 μg/mL）。尽管最活跃的化合物具有良好的理化性质，其中一种与小鼠肝微粒体一起孵育时的半衰期约为 3 小时，但两种代表性的高活性化合物对半胱氨酸衍生物表现出强烈的化学反应性，作为体内替代物以硫为中心的亲核试剂，表明亲电性过高，因此可能在体内发生不加区别的化学反应，代表一般毒性的不可接受的高风险，并且治疗有效的可能性很低。