6-(2-thienyl)-3-thioxo-2,3,4,5-tetrahydro-1,2,4-triazin-5-one | 27623-07-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 6-(2-thienyl)-3-thioxo-2,3,4,5-tetrahydro-1,2,4-triazin-5-one
• 英文别名: 6-thiophen-2-yl-3-thioxo-3,4-dihydro-2H-[1,2,4]triazin-5-one；6-[2]thienyl-3-thioxo-3,4-dihydro-2H-[1,2,4]triazin-5-one；6-[2]Thienyl-3-thioxo-3,4-dihydro-2H-[1,2,4]triazin-5-on；6-(2-Thienyl)-2,3,4,5-tetrahydro-as-triazin-5-on-3-thion；6-(thiophen-2-yl)-3-thioxo-3,4-dihydro-1,2,4-triazin-5(2H)-one；3-sulfanylidene-6-thiophen-2-yl-2H-1,2,4-triazin-5-one
• CAS: 27623-07-0
• 化学式: C₇H₅N₃OS₂
• mdl: MFCD01918431
• 分子量: 211.268
• InChiKey: YDOAVONEZJKTNW-UHFFFAOYSA-N

物化性质

• 密度：
  1.72±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(2-thienyl)-3-thioxo-2,3,4,5-tetrahydro-1,2,4-triazin-5-one 在 吡啶 、 sodium methylate 、 氯乙酸 、 六甲基二硅氮烷 作用下， 以 甲醇 、 氯仿 、 水 为溶剂， 反应 30.0h， 生成
  参考文献：
  名称：

  The Synthesis of Some 5-Substituted-6-aza-2′-deoxyuridines

  摘要：

  5-(2-Thienyl)-1-(2-deoxy-3,5-di-O-p-toluoyl-beta-D-erythro-pentofuranosyl)-6-azauracil [VIII] and 5-cyclopropyl-1-(2-deoxy-3,5-di-O-p-toluoyl-beta-D-erythro-pentofuranosyl)-6-azauracil [X] were obtained in high yields (93.5% and 81.3% respectively) exclusively as beta anomers, by condensation of the corresponding silylated triazine bases with 2-deoxy-3,5-di-O-p-toluoyl-D-erythro-pentosyl chloride in chloroform. After deblocking both nucleosides with sodium methoxide in methanol, 5-(2-thienyl)-6-aza-2'-deoxyuridine [IX] and 5-cyclopropyl-6-aza-2'-deoxyuridine [XI] were obtained. The nucleoside IX was further acetylated, brominated with Br-2/CCl4 and deblocked with methanolic ammonia to give 6-aza-5[2-(5-bromothienyl)]-2'-deoxyuridine [XIV].

  DOI：

  10.1080/15257779408013233
• 作为产物：
  描述：

  2-噻吩乙醛酸 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 33.0h， 生成 6-(2-thienyl)-3-thioxo-2,3,4,5-tetrahydro-1,2,4-triazin-5-one
  参考文献：
  名称：

  The Synthesis of Some 5-Substituted-6-aza-2′-deoxyuridines

  摘要：

  5-(2-Thienyl)-1-(2-deoxy-3,5-di-O-p-toluoyl-beta-D-erythro-pentofuranosyl)-6-azauracil [VIII] and 5-cyclopropyl-1-(2-deoxy-3,5-di-O-p-toluoyl-beta-D-erythro-pentofuranosyl)-6-azauracil [X] were obtained in high yields (93.5% and 81.3% respectively) exclusively as beta anomers, by condensation of the corresponding silylated triazine bases with 2-deoxy-3,5-di-O-p-toluoyl-D-erythro-pentosyl chloride in chloroform. After deblocking both nucleosides with sodium methoxide in methanol, 5-(2-thienyl)-6-aza-2'-deoxyuridine [IX] and 5-cyclopropyl-6-aza-2'-deoxyuridine [XI] were obtained. The nucleoside IX was further acetylated, brominated with Br-2/CCl4 and deblocked with methanolic ammonia to give 6-aza-5[2-(5-bromothienyl)]-2'-deoxyuridine [XIV].

  DOI：

  10.1080/15257779408013233

文献信息

• WO2007/17114
  申请人：——

  公开号：——

  公开（公告）日：——
• Hagenbach et al., Angewandte Chemie, 1954, vol. 66, p. 359,361
  作者：Hagenbach et al.

  DOI：——

  日期：——
• [EN] NEW SUBSTITUTED AZATHYMIDINE DERIVATIVES AND THEIR USE IN THE TREATMENT OF BACTERIAL INFECTIOUS DISEASES<br/>[FR] NOUVEAUX DERIVES D'AZATHYMIDINE SUBSTITUES ET LEUR UTILISATION DANS LE TRAITEMENT DE MALADIES INFECTIEUSES BACTERIENNES
  申请人：ATHELAS S A

  公开号：WO2007017114A1

  公开（公告）日：2007-02-15

  [EN] The invention relates to substituted azathymidines and related compounds of formula (I), wherein X is N or CH, and R¹, R² and R³ are as described in the specification, processes for the preparation thereof, pharmaceutical compositions containing the same, the use thereof optionally in combination with one or more other pharmaceutically active compounds as antibacterial agents for the therapy of infective diseases, and a method for the treatment of such diseases. The compounds of formula (I) are reducing selectively the pathogenicity of bacteria within the host, but without affecting the bacteria outside the host environment.
  [FR] L'invention concerne des azathymidines substituées et des composés connexes de la formule (I), dans laquelle X représente N ou CH, et R¹, R² et R³ sont tels que spécifiés dans le descriptif, leurs processus de préparation, des compositions pharmaceutiques les renfermant, leur utilisation éventuellement en combinaison avec un ou plusieurs autres composés pharmaceutiquement actifs comme agents antibactériens pour le traitement de maladies infectieuses, ainsi qu'un procédé de traitement de ces maladies. Les composés de la formule (I) réduisent de manière sélective la pathogénicité des bactéries chez l'hôte, sans affecter les bactéries hors de l'environnement hôte.