4-amino-6-(4-chlorobenzyl)-3-methylthio-4,5-dihydro-1,2,4-triazin-5-one | 22285-39-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-amino-6-(4-chlorobenzyl)-3-methylthio-4,5-dihydro-1,2,4-triazin-5-one
• 英文别名: 3-methylthio-4-amino-6-(4'-chlorobenzyl)-1,2,4-triazine-5-one；4-amino-6-(4-chlorobenzyl)-3-(methylsulfanyl)-1,2,4-triazin-5(4H)-one；4-amino-6-[(4-chlorophenyl)methyl]-3-methylsulfanyl-1,2,4-triazin-5-one
• CAS: 22285-39-8
• 化学式: C₁₁H₁₁ClN₄OS
• 分子量: 282.754
• InChiKey: CMDMHIUVJPSRDE-UHFFFAOYSA-N

物化性质

• 熔点：
  190 °C(Solv: ethanol (64-17-5))
• 沸点：
  434.4±47.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  96.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-amino-6-(4-chlorobenzyl)-3-methylthio-4,5-dihydro-1,2,4-triazin-5-one 在 吡啶 、 一水合肼 作用下， 以 异丙醇 为溶剂， 反应 6.0h， 生成 8-amino-6-(4-chlorobenzyl)-2,8-dihydro-3-thioxo-1,2,4-triazolo[4,3-b][1,2,4]-triazin-7(3H)-one
  参考文献：
  名称：

  Synthesis of Some Novel 6‐Benzyl(or Substituted Benzyl)‐2‐β‐d‐Glucopyranosyl‐1,2,4‐Triazolo[4,3‐b][1,2,4]Triazines as Potential Antimicrobial Chemotherapeutics

  摘要：

  Glucosidation of the new 8-amino-6-benzyl(or substituted benzyl)-2,8-dihydro-1,2,4tri azolo [4,3-b] [1,2,4]triazin-7(3 H)-ones (3a-d) with 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide 4 gave the corresponding N-glucosides 5a-d. Chemical transformations leading to new functionalities have also been achieved to give compounds 7-12. Antimicrobial activity of compounds 5a-c against Aspergillus fumigatus, Penicillium italicum, Syncephalastrum racemosum, Candida albicans, Staphylococcus aureus, Pseudomonas aeruginosa, Bacillus subtilis, Escherichia coli is described.

  DOI：

  10.1081/ncn-200040663
• 作为产物：
  描述：

  4-amino-6-(4-chlorobenzyl)-3-thioxo-2,3-dihydro-1,2,4-triazin-5(4H)-one 、 碘甲烷 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以89%的产率得到4-amino-6-(4-chlorobenzyl)-3-methylthio-4,5-dihydro-1,2,4-triazin-5-one
  参考文献：
  名称：

  Synthesis of Some Novel 6‐Benzyl(or Substituted Benzyl)‐2‐β‐d‐Glucopyranosyl‐1,2,4‐Triazolo[4,3‐b][1,2,4]Triazines as Potential Antimicrobial Chemotherapeutics

  摘要：

  Glucosidation of the new 8-amino-6-benzyl(or substituted benzyl)-2,8-dihydro-1,2,4tri azolo [4,3-b] [1,2,4]triazin-7(3 H)-ones (3a-d) with 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide 4 gave the corresponding N-glucosides 5a-d. Chemical transformations leading to new functionalities have also been achieved to give compounds 7-12. Antimicrobial activity of compounds 5a-c against Aspergillus fumigatus, Penicillium italicum, Syncephalastrum racemosum, Candida albicans, Staphylococcus aureus, Pseudomonas aeruginosa, Bacillus subtilis, Escherichia coli is described.

  DOI：

  10.1081/ncn-200040663

文献信息

• Synthesis, reactions and biological evaluation of some 1,2,4-triazine derivatives
  作者：A. K. Mansour、Mohga M. Eid、R. A. Hassan、A. Haemers、S. R. Pattyn、D. A. Vanden Berghe、L. Van Hoof

  DOI：10.1002/jhet.5570250146

  日期：1988.1

  react with hydrazine hydrate to give the corresponding 6-substituted benzyl-4-amino-2,3,4,5-tetrahydro-1,2,4-triazin-3,5-diones 10a-c. The biological evaluation of some of these triazines is described. All compounds were screened for antiviral, antibacterial, antimycobacterial, antifungal and antiyeast activity. No important biological activity was found.

  制备6-取代的苄基-4-苯基-3-硫代氧代2,3,4,5-四氢-1,2,4-三嗪-5-酮3a-d并将其转化为它们相应的3-甲硫基衍生物4a- d。化合物4a-d与水合肼的反应得到相应的4-氨基-3-苯胺基-4,5-二氢-1,2,4-三嗪-5-酮5a-d。合成6-取代的苄基-4-苯基-2,3,4,5-四氢-1,2,4-三嗪-3,5-二酮9a-c，并使其与水合肼反应，得到相应的6--取代的苄基-4-氨基-2,3,4,5-四氢-1,2,4-三嗪-3,5-二酮10a-c。描述了其中一些三嗪的生物学评估。筛选所有化合物的抗病毒，抗菌，抗分枝杆菌，抗真菌和抗酵母活性。没有发现重要的生物学活性。
• MANSOUR, A. K.;EID, MOHGA M.;HASSAN, R. A.;HAEMERS, A.;PATTYN, S. R.;VAND+, J. HETEROCYCL. CHEM., 25,(1988) N 1, 279-283
  作者：MANSOUR, A. K.、EID, MOHGA M.、HASSAN, R. A.、HAEMERS, A.、PATTYN, S. R.、VAND+

  DOI：——

  日期：——
• US3961936A
  申请人：——

  公开号：US3961936A

  公开（公告）日：1976-06-08
• US3966715A
  申请人：——

  公开号：US3966715A

  公开（公告）日：1976-06-29
• US4036632A
  申请人：——

  公开号：US4036632A

  公开（公告）日：1977-07-19