6-Amino-4-methyl-3-methylthio-1,2,4-triazin-5(4H)-on | 89730-72-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 6-Amino-4-methyl-3-methylthio-1,2,4-triazin-5(4H)-on
• 英文别名: 6-amino-4-methyl-3-(methylthio)-1,2,4-triazin-5(4H)-one；6-amino-4-methyl-3-methylsulfanyl-4H-[1,2,4]triazin-5-one；6-amino-4-methyl-3-methylthio-1,2,4-triazin-5-one；6-Amino-4-methyl-3-(methylsulfanyl)-1,2,4-triazin-5(4H)-one；6-amino-4-methyl-3-methylsulfanyl-1,2,4-triazin-5-one
• CAS: 89730-72-3
• 化学式: C₅H₈N₄OS
• 分子量: 172.211
• InChiKey: QJHAMNQWHLGESW-UHFFFAOYSA-N

物化性质

• 沸点：
  284.4±23.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  96.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-Amino-4-methyl-3-methylthio-1,2,4-triazin-5(4H)-on 在 氢溴酸 、 碳酸氢钠 作用下， 以 异丙醇 为溶剂， 生成 3-methyl-2-methylsulfanyl-3H-imidazo[2,1-f][1,2,4]triazin-4-one
  参考文献：
  名称：

  Imidazo[1,2-a]pyrazin-8-ones, imidazo[1,2-d][1,2,4]triazin-8-ones and imidazo[2,1-f][1,2,4]triazin-8-ones as α2/α3 subtype selective GABAA agonists for the treatment of anxiety

  摘要：

  Imidazo[1,2-a]pyrazin-8-ones, imidazo[1, 2-d] [ 1, 2,4]triazin-8 -ones and imidazo[2,1-f][1,2,4]triazin-8-ones are high affinity GABA(A) agonists. Compound 16d has good oral bioavailability in rat, functional selectivity for the GABA(A) alpha 2 and alpha 3-subtypes and is anxiolytic in a conditioned animal model of anxiety with minimal sedation observed at full BZ binding site occupancy. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.12.027
• 作为产物：
  描述：

  硫代草氨酸乙酯 、 3-methylthio-4-methyl semicarbazide hydroiodide 在 三乙胺 作用下， 以 乙醇 为溶剂， 以47%的产率得到6-Amino-4-methyl-3-methylthio-1,2,4-triazin-5(4H)-on
  参考文献：
  名称：

  Neunhoeffer, Hans; Hammann, Heinz, Liebigs Annalen der Chemie, 1984, # 2, p. 283 - 295

  摘要：

  DOI：

文献信息

• Imidazotriazinone derivatives as ligands for GABA receptors
  申请人：——

  公开号：US20040235844A1

  公开（公告）日：2004-11-25

  The present invention relates to imidazo[2,1-f]triazin-4-one analogues which are substituted in the 7-position by a substituted phenyl ring, being ligands for GABA A receptors and accordingly of benefit in the therapy of deleterious neurological disorders.

  本发明涉及在7位被取代苯环取代的咪唑[2,1-f]三唑-4-酮类似物，它们是GABA A 受体的配体，因此在治疗有害神经系统疾病方面具有益处。
• Aminopyrazinones and aminotriazinones
  申请人：——

  公开号：US04795486A1

  公开（公告）日：1989-01-03

  Aminopyrazinones and aminotriazinones of the formula ##STR1## and the salts of these compounds with amines, alkali metal or alkaline earth metal bases or quaternary ammonium bases have good pre- and post-emergent selective herbicidal and growth-regulating properties. In this formula, E is nitrogen or .dbd.CR.sup.4 --, R.sup.1 is C.sub.1 -C.sub.4 -alkyl, R.sup.2 is hydrogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -halogenoalkyl, C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.3 -halogenoalkoxy, C.sub.1 -C.sub.3 -alkylthio, C.sub.1 -C.sub.3 -alkylsulfinyl, C.sub.1 -C.sub.2 -alkoxyethoxy, C.sub.1 -C.sub.3 -alkylsulfonyl, halogen or --NR.sup.5 R.sup.6, R.sup.3 is hydrogen or C.sub.1 -C.sub.3 -alkyl and Q is a group ##STR2## in which R.sup.4 is hydrogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -halogenoalkyl, C.sub.1 -C.sub.3 -alkoxy, cyclopropyl, C.sub.1 -C.sub.3 -halogenoalkoxy, C.sub.1 -C.sub.3 -alkylthio, C.sub.2 -C.sub.4 -alkoxyalkyl, C.sub.3 -C.sub.5 -dialkoxymethyl, halogen or --NR.sup.5 R.sup.6, R.sup.5 and R.sup.6 independently of one another are hydrogen or C.sub.1 -C.sub.3 -alkyl, X is oxygen or sulfur and A is a group ##STR3## in which Y is oxygen, sulfur, --CH.dbd.CH--, --NR.sup.9 -- or --CR.sup.10 .dbd.N--, R.sup.7 is hydrogen, halogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -alkoxy, nitro or trifluoromethyl, R.sup.8 is hydrogen, halogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -alkoxy, nitro, --C.dbd.CH, or one of the groups ##STR4## R.sup.9 and R.sup.10 independently of one another are hydrogen, C.sub.1 -C.sub.3 -alkyl or C.sub.2 -C.sub.4 -alkenyl, R.sup.11 is hydrogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -halogenoalkyl, C.sub.3 -C.sub.6 -cycloalkyl or C.sub.2 -C.sub.4 -alkoxyalkyl, R.sup.12 is C.sub.1 -C.sub.6 -alkoxy, C.sub.3 -C.sub.6 -alkenyloxy, C.sub.3 -C.sub.6 -alkinyloxy, C.sub.2 -C.sub.6 -halogenoalkoxy, C.sub.1 -C.sub.4 -cyanoalkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.3 -C.sub.6 -alkenylthio, C.sub.3 -C.sub.6 -alkinylthio, C.sub.5 -C.sub.6 -cycloalkoxy, C.sub.2 -C.sub.6 -alkoxyalkoxy or --NR.sup.16 R.sup.17, R.sup.13 is hydrogen, C.sub.1 -C.sub.3 -alkyl or C.sub.3 -C.sub.4 -alkenyl, R.sup.14 is hydrogens C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -cyanoalkyl or C.sub.1 -C.sub.3 -alkoxy, R.sup.15 is C.sub.3 -C.sub.6 -alkinyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -halogenoalkyl, C.sub. 2 -C.sub.4 -halogenoalkenyl or C.sub.1 -C.sub.4 -alkyl, substituted by cyano, methoxy, ethoxy, nitro, C.sub.1 -C.sub.4 -alkoxycarbonyl, methylthio, ethylthio, methylsulfonyl or ethylsulfonyl; or C.sub.3 -C.sub.4 -alkenyl substituted by nitro, cyano, methoxy or ethoxy, R.sup.16 is hydrogen, C.sub.1 -C.sub.3 -alkyl or C.sub.3 -C.sub.4 -alkenyl, R.sup.17 is hydrogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -cyanoalkyl or C.sub.1 -C.sub.3 -alkoxy, R.sup.18 is C.sub.1 -C.sub.3 -alkyl and C.sub.1 -C.sub.3 -halogenoalkyl, W is oxygen or sulfur, Z is oxygen, sulfur, --SO-- or --SO.sub.2 -- and m is the number zero or one.

  Aminopyrazinones和aminotriazinones的化学式为##STR1##，以及这些化合物与胺、碱金属或碱土金属碱或季铵盐的盐具有良好的前后除草和生长调节性能。在这个化学式中，E是氮或.dbd.CR.sup.4 --，R.sup.1是C.sub.1 -C.sub.4 -烷基，R.sup.2是氢、C.sub.1 -C.sub.3 -烷基、C.sub.1 -C.sub.3 -卤代烷基、C.sub.1 -C.sub.3 -氧烷基、C.sub.1 -C.sub.3 -卤代氧烷基、C.sub.1 -C.sub.3 -硫烷基、C.sub.1 -C.sub.3 -烷基亚硫醇、C.sub.1 -C.sub.2 -氧烷氧基、C.sub.1 -C.sub.3 -烷基磺酰基、卤素或--NR.sup.5 R.sup.6，R.sup.3是氢或C.sub.1 -C.sub.3 -烷基，Q是一个基团##STR2##，其中R.sup.4是氢、C.sub.1 -C.sub.3 -烷基、C.sub.1 -C.sub.3 -卤代烷基、C.sub.1 -C.sub.3 -氧烷基、环丙基、C.sub.1 -C.sub.3 -卤代氧烷基、C.sub.1 -C.sub.3 -硫烷基、C.sub.2 -C.sub.4 -氧烷基、C.sub.3 -C.sub.5 -二烷氧甲基、卤素或--NR.sup.5 R.sup.6，R.sup.5和R.sup.6彼此独立地是氢或C.sub.1 -C.sub.3 -烷基，X是氧或硫，A是一个基团##STR3##，其中Y是氧、硫、--CH.dbd.CH--、--NR.sup.9 --或--CR.sup.10 .dbd.N--，R.sup.7是氢、卤素、C.sub.1 -C.sub.3 -烷基、C.sub.1 -C.sub.3 -氧烷基、硝基或三氟甲基，R.sup.8是氢、卤素、C.sub.1 -C.sub.3 -烷基、C.sub.1 -C.sub.3 -氧烷基、硝基、--C.dbd.CH，或以下基团之一##STR4##，R.sup.9和R.sup.10彼此独立地是氢、C.sub.1 -C.sub.3 -烷基或C.sub.2 -C.sub.4 -烯基，R.sup.11是氢、C.sub.1 -C.sub.3 -烷基、C.sub.1 -C.sub.3 -卤代烷基、C.sub.3 -C.sub.6 -环烷基或C.sub.2 -C.sub.4 -氧烷基，R.sup.12是C.sub.1 -C.sub.6 -氧烷基、C.sub.3 -C.sub.6 -烯氧基、C.sub.3 -C.sub.6 -炔氧基、C.sub.2 -C.sub.6 -卤代氧烷基、C.sub.1 -C.sub.4 -氰基氧烷基、C.sub.1 -C.sub.6 -硫烷基、C.sub.3 -C.sub.6 -烯基硫、C.sub.3 -C.sub.6 -炔基硫、C.sub.5 -C.sub.6 -环烷氧基、C.sub.2 -C.sub.6 -氧烷氧基或--NR.sup.16 R.sup.17，R.sup.13是氢、C.sub.1 -C.sub.3 -烷基或C.sub.3 -C.sub.4 -烯基，R.sup.14是氢、C.sub.1 -C.sub.3 -烷基、C.sub.1 -C.sub.3 -氰基烷基或C.sub.1 -C.sub.3 -氧烷基，R.sup.15是C.sub.3 -C.sub.6 -炔基、C.sub.2 -C.sub.6 -烯基、C.sub.1 -C.sub.6 -烷基、C.sub.1 -C.sub.4 -卤代烷基、C.sub. 2 -C.sub.4 -卤代烯基或C.sub.1 -C.sub.4 -烷基，通过氰基、甲氧基、乙氧基、硝基、C.sub.1 -C.sub.4 -氧基羰基、甲硫基、乙硫基、甲基磺酰基或乙基磺酰基取代；或通过硝基、氰基、甲氧基或乙氧基取代的C.sub.3 -C.sub.4 -烯基，R.sup.16是氢、C.sub.1 -C.sub.3 -烷基或C.sub.3 -C.sub.4 -烯基，R.sup.17是氢、C.sub.1 -C.sub.3 -烷基、C.sub.1 -C.sub.3 -氰基烷基或C.sub.1 -C.sub.3 -氧烷基，R.sup.18是C.sub.1 -C.sub.3 -烷基和C.sub.1 -C.sub.3 -卤代烷基，W是氧或硫，Z是氧、硫、--SO--或--SO.sub.2 --，m是数字零或一。
• Aminopyrazinones
  申请人：Ciba-Geigy Corporation

  公开号：US04871853A1

  公开（公告）日：1989-10-03

  Aminopyrazinones and aminotriazinones of the formula ##STR1## and the salts of these compounds with amines, alkali metal or alkaline earth metal bases or quaternary ammonium bases have good pre- and post-emergent selective herbicidal and growth-regulating properties. In this formula, E is nitrogen or .dbd.CR.sup.4 --, R.sup.1 is C.sub.1 -C.sub.4 -alkyl, R.sup.2 is hydrogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -halogenoalkyl, C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.3 -halogenoalkoxy, C.sub.1 -C.sub.3 -alkylthio, C.sub.1 -C.sub.3 -alkylsulfinyl, C.sub.1 -C.sub.2 -alkoxyethoxy, C.sub.1 -C.sub.3 -alkylsulfonyl, halogen or --NR.sup.5 R.sup.6, R.sup.3 is hydrogen or C.sub.1 -C.sub.3 -alkyl and Q is a group ##STR2## in which R.sup.4 is hydrogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -halogenoalkyl, C.sub.1 -C.sub.3 -alkoxy, cyclopropyl, C.sub.1 -C.sub.3 -halogenoalkoxy, C.sub.1 -C.sub.3 -alkylthio, C.sub.2 -C.sub.4 -alkoxyalkyl, C.sub.3 -C.sub.5 -dialkoxymethyl, halogen or --NR.sup.5 R.sup.6, R.sup.5 and R.sup.6 independently of one another are hydrogen or C.sub.1 -C.sub.3 -alkyl, X is oxygen or sulfur and A is a group ##STR3## in which Y is oxygen, sulfur, --CH.dbd.CH--, -- NR.sup.9 --or --CR.sup.10 .dbd.N--, R.sup.7 is hydrogen, halogen, C.sub.1 -C.sub.3 -alkyl C.sub.1 -C.sub.3 -alkoxy, nirtro or trifluoromethyl, R.sup.8 is hydrogen, halogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 -alkoxy, nitro --C.tbd.CH, or one of the groups R.sup.9 and R.sup.10 independently of one another are hydrogen, C.sub.1 -C.sub.3 -alkyl or C.sub.2 -C.sub.4 -alkenyl, R.sup.11 is hydrogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -halogenoalkyl, C.sub.3 -C.sub.6 -cycloalkyl or C.sub.2 -C.sub.4 -alkoxyalkyl, R.sup.12 is C.sub.1 -C.sub.6 -alkoxy, C.sub.3 -C.sub.6 -alkenyloxy, C.sub.3 -C.sub.6 -alkenyloxy, C.sub.3 -C.sub.6 -alkinyloxy, C.sub.2 -C.sub.6 -halogenoalkoxy, C.sub.1 -C.sub.4 -cyanoalkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.3 -C.sub.6 -alkenylthio, C.sub.3 -C.sub.6 -alkinylthio, C.sub.5 -C.sub.6 -cycloalkoxy, C.sub.2 -C.sub.6 -alkoxyalkoxy or --NR.sup.16 R.sup.17, R.sup.13 is hydrogen, C.sub.1 -C.sub.3 -alkyl or C.sub.3 -C.sub.4 -alkenyl, R.sup.14 is hydrogens C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -cyanoalkyl or C.sub.1 -C.sub.3 -alkoxy, R.sup.15 is C.sub.3 -C.sub.6 -alkinyl,C.sub.2 -C.sub.6 -alkenyl, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub. 4 -halogenoalkyl, C.sub.2 -C.sub.4 -halogenoalkenyl or C.sub.1 -C.sub.4 -alkyl, substituted by cyano, methoxy, ethoxy, nitro, C.sub.1 -C.sub.4 -alkoxycarbonyl, methylthio, ethylthio, methylsulfonyl or ethylsulfonyl; or C.sub.3 -C.sub.4 -alkenyl substituted by nitro, cyano, methoxy or ethoxy, R.sup.16 is hydrogen, C.sub.1 -C.sub.3 -alkyl or C.sub.3 -C.sub.4 -alkenyl, R.sup.17 is hydrogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -cyanoalkyl or C.sub.1 -C.sub.3 -alkoxy, R.sup.18 is C.sub.1 -C.sub.3 -alkyl and C.sub.1 -C.sub.3 -halogenoalkyl, W is oxygen or sulfur, Z is oxygen, sulfur, --SO-- or --SO.sub.2 -- and m is the number zero or one.

  式为##STR1##的氨基吡嗪酮和氨基三嗪酮以及这些化合物与胺、碱金属或碱土金属碱或季铵碱的盐具有良好的前、后除草和生长调节性能。在这个式子中，E是氮或.dbd.CR.sup.4 --，R.sup.1是C.sub.1-C.sub.4-烷基，R.sup.2是氢、C.sub.1-C.sub.3-烷基、C.sub.1-C.sub.3-卤代烷基、C.sub.1-C.sub.3-烷氧基、C.sub.1-C.sub.3-卤代烷氧基、C.sub.1-C.sub.3-烷基硫基、C.sub.1-C.sub.3-烷基亚砜基、C.sub.1-C.sub.2-烷氧基乙氧基、C.sub.1-C.sub.3-烷基磺酰基、卤素或--NR.sup.5 R.sup.6，R.sup.3是氢或C.sub.1-C.sub.3-烷基，Q是一个基团##STR2##其中R.sup.4是氢、C.sub.1-C.sub.3-烷基、C.sub.1-C.sub.3-卤代烷基、C.sub.1-C.sub.3-烷氧基、环丙基、C.sub.1-C.sub.3-卤代烷氧基、C.sub.1-C.sub.3-烷基硫基、C.sub.2-C.sub.4-烷氧基烷基、C.sub.3-C.sub.5-二烷氧甲基、卤素或--NR.sup.5 R.sup.6，R.sup.5和R.sup.6彼此独立地是氢或C.sub.1-C.sub.3-烷基，X是氧或硫，A是一个基团##STR3##其中Y是氧、硫、--CH.dbd.CH--、--NR.sup.9--或--CR.sup.10.dbd.N--，R.sup.7是氢、卤素、C.sub.1-C.sub.3-烷基、C.sub.1-C.sub.3-烷氧基、硝基或三氟甲基，R.sup.8是氢、卤素、C.sub.1-C.sub.3-烷基、C.sub.1-C.sub.3-烷氧基、硝基、--C.tbd.CH或其中之一R.sup.9和R.sup.10独立地是氢、C.sub.1-C.sub.3-烷基或C.sub.2-C.sub.4-烯基，R.sup.11是氢、C.sub.1-C.sub.3-烷基、C.sub.1-C.sub.3-卤代烷基、C.sub.3-C.sub.6-环烷基或C.sub.2-C.sub.4-烷氧基烷基，R.sup.12是C.sub.1-C.sub.6-烷氧基、C.sub.3-C.sub.6-烯氧基、C.sub.3-C.sub.6-炔氧基、C.sub.2-C.sub.6-卤代烷氧基、C.sub.1-C.sub.4-氰基烷氧基、C.sub.1-C.sub.6-烷基硫氧基、C.sub.3-C.sub.6-烯基硫氧基、C.sub.3-C.sub.6-炔基硫氧基、C.sub.5-C.sub.6-环烷氧基、C.sub.2-C.sub.6-烷氧基烷氧基或--NR.sup.16 R.sup.17，R.sup.13是氢、C.sub.1-C.sub.3-烷基或C.sub.3-C.sub.4-烯基，R.sup.14是氢、C.sub.1-C.sub.3-烷基、C.sub.1-C.sub.3-氰基烷基或C.sub.1-C.sub.3-烷氧基，R.sup.15是C.sub.3-C.sub.6-炔基、C.sub.2-C.sub.6-烯基、C.sub.1-C.sub.6-烷基、C.sub.1-C.sub.4-卤代烷基、C.sub.2-C.sub.4-卤代烯基或C.sub.1-C.sub.4-烷基，通过氰基、甲氧基、乙氧基、硝基、C.sub.1-C.sub.4-烷氧羰基、甲硫基、乙硫基、甲磺酰基或乙磺酰基取代；或C.sub.3-C.sub.4-烯基通过硝基、氰基、甲氧基或乙氧基取代，R.sup.16是氢、C.sub.1-C.sub.3-烷基或C.sub.3-C.sub.4-烯基，R.sup.17是氢、C.sub.1-C.sub.3-烷基、C.sub.1-C.sub.3-氰基烷基或C.sub.1-C.sub.3-烷氧基，R.sup.18是C.sub.1-C.sub.3-烷基和C.sub.1-C.sub.3-卤代烷基，W是氧或硫，Z是氧、硫、--SO--或--SO.sub.2--，m是数字零或一。
• NEUNHOEFFER, H.;HAMMANN, H., LIEBIGS ANN. CHEM., 1984, N 2, 283-295
  作者：NEUNHOEFFER, H.、HAMMANN, H.

  DOI：——

  日期：——
• WO2024099993A1
  申请人：——

  公开号：——

  公开（公告）日：——