2-mercapto-7-methyl-5-oxo-5H-1,3,4-thiadiazolo[3,2-a]pyrimidine | 68967-31-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-mercapto-7-methyl-5-oxo-5H-1,3,4-thiadiazolo[3,2-a]pyrimidine
• 英文别名: 7-methyl-2-thioxo-2,3-dihydro-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one；2-mercapto-7-methyl-5-oxo-5H-1,3,4thiadiazolo[3,2-a]pyrimidine；7-methyl-2-sulfanyl-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one；7-methyl-2-sulfanylidene-3H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one
• CAS: 68967-31-7
• 化学式: C₆H₅N₃OS₂
• mdl: MFCD01626699
• 分子量: 199.257
• InChiKey: IRUKGGHQKGTAPN-UHFFFAOYSA-N

物化性质

• 熔点：
  121-123 °C(Solv: water (7732-18-5))
• 沸点：
  305.1±25.0 °C(Predicted)
• 密度：
  1.78±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-mercapto-7-methyl-5-oxo-5H-1,3,4-thiadiazolo[3,2-a]pyrimidine 生成 disodium;(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[carboxy-(3,4-dihydroxyphenyl)methoxy]iminoacetyl]amino]-3-[(5-carboxylato-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
  参考文献：
  名称：

  OHNISHI, HARUO;KOSUZUME, HIROSHI;MIZOTA, MASAHIRO;SUZUKI, YASUO;MOCHIDA, +

  摘要：

  DOI：
• 作为产物：
  描述：

  2-bromo-7-methyl-5-oxo-5H-1,3,4-thiadiazolo<3,2-a>pyrimidine 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 生成 2-mercapto-7-methyl-5-oxo-5H-1,3,4-thiadiazolo[3,2-a]pyrimidine
  参考文献：
  名称：

  Reactions of thioamides and alkali metal salts of dithiocarbamates with 2-bromo-7-methyl-5-oxo-5H-1,3,4-thiazolo[3,2-a]pyrimidine and antimicrobial activity of products

  摘要：

  通过各种硫代酰胺与 2-溴-7-甲基-5-氧代-5H-1,3,4-噻唑并[3,2-a]嘧啶的反应，合成了一系列硫脲盐。这些产品具有抗菌活性。

  DOI：

  10.1007/s11094-006-0144-1

文献信息

• Cephalosporin derivatives
  申请人：Mochida Pharmaceutical Co., Ltd.

  公开号：US04840945A1

  公开（公告）日：1989-06-20

  The present invention relates to novel cephalosporin derivatives, processes for preparing thereof, compositions for preventing and/or treating infectious diseases which comprise the novel cephalosporin derivatives as active components, and the intermediate compounds in the synthesis of cephalosporin derivatives and processes for producing thereof. The present invention is based on the selection of groups containing a condensed heterocyclic ring, particularly a triazolopyrimidine ring or a thiadiazolopyrimidine ring, as substituents at the 3-position of the cephem skeleton, and of groups containing a catechol moiety, particularly a catechol carboxymethyloxyimino moiety or a catechol carboxyimino moiety, as substituents at the 7-position of the cephem skeleton. The compounds of the present invention containing the aforementioned substituents have a strong antibacterial activity against Gram-negative bacteria and also against Gram-positive bacteria including methicillin-resistant Staphylococcus aureus. These compounds are extremely useful for the treatment of infectious diseases.

  本发明涉及新型头孢菌素衍生物，其制备方法，包含新型头孢菌素衍生物作为活性成分的预防和/或治疗传染病的组合物，以及头孢菌素衍生物合成中的中间化合物和其生产方法。本发明基于在头孢菌素骨架的3位选择含有紧凑杂环环，特别是三唑嘧啶环或噻二唑嘧啶环的基团，作为取代基，以及在头孢菌素骨架的7位选择含有邻苯二酚基团，特别是邻苯二酚羧甲氧基亚胺基团或邻苯二酚羧亚胺基团作为取代基。本发明中含有上述取代基的化合物对革兰氏阴性细菌和包括耐甲氧苄青霉素金黄色葡萄球菌在内的革兰氏阳性细菌具有强大的抗菌活性。这些化合物对于治疗传染病非常有用。
• Syntheses and reactions of N-aminothiouracils and thiadiazolo[3,2-.ALPHA.]pyrimidinones.
  作者：TADAKAZU TSUJI、YOSHIMI OTSUKA

  DOI：10.1248/cpb.26.2765

  日期：——

  3-Amino-6-methyluracil and its thio analogs were synthesized. From these thio analogs, 7-methyl-5H-1, 3, 4-thiadiazolo [3, 2-α] pyrimidin-5-one, its 2-amino and 2- or 5-thio derivatives were prepared. Reflux of thiadiazolopyrimidines with chloroacetic acid or hydrochloric acid led to the ring opening of the thiadiazole moiety to give unexpected 3-amino-6-methyluracil.

  合成了 3-氨基-6-甲基尿嘧啶及其硫代类似物。从这些硫代类似物中，制备出了 7-甲基-5H-1, 3, 4-噻二唑并[3, 2-α] 嘧啶-5-酮及其 2-氨基和 2-或 5-硫代衍生物。噻二唑并嘧啶与氯乙酸或盐酸回流，导致噻二唑分子开环，得到意想不到的 3-氨基-6-甲基尿嘧啶。
• [EN] CEPHALOSPORIN DERIVATIVES
  申请人：MOCHIDA PHARMACEUTICAL CO., LTD.

  公开号：WO1986005786A1

  公开（公告）日：1986-10-09

  (EN) Novel cephalosporin derivatives, processes for preparing thereof, compositions for preventing and/or treating infectious diseases which comprise the novel cephalosporin derivatives as active components, and the intermediate compounds in the synthesis of cephalosporin derivatives and processes for producing thereof. The present invention is based on the selection of groups containing a condensed heterocyclic ring, particularly a triazolopyrimidine ring or a thiadiazolopyrimidine ring, as substituents at the 3-position of the cephem skeleton, and of groups containing a catechol moiety, particularly a catechol carboxymethyloxyimino moiety or a catechol carboxyimino moiety, as substituents at the 7-position of the cephem skeleton. The compounds of the present invention containing the aforementioned substituents have a strong antibacterial activity against Gram-negative bacteria and also against Gram-positive bacteria including methicillin-resistant $i(Staphylococcus aureus). These compounds are extremely useful for the treatment of infectious diseases.(FR) Nouveaux dérivés de céphalosporine, leurs procédés de préparation, compositions permettant de prévenir et/ou de traiter des maladies infectieuses et comportant les nouveaux dérivés de céphalosporine comme constituants actifs, ainsi que composés intermédiaires dans la synthèse des dérivés de céphalosporine et leurs procédés de préparation. La présente invention est fondée sur la sélection de groupes contenant un noyau hétérocyclique condensé, notamment un noyau de triazolopyrimidine ou un noyau de thiadiazolopyrimide, sous forme de substituants en position 3 du squelette de céphème, et de groupes contenant une fraction catéchol, en particulier une partie carboxyméthyloxyimino de catéchol ou une partie carboxymino de catéchol, sous forme de substituants en position 7 du squelette du céphème. Les composés ci-décrits contenant les substituants précités possèdent une forte activité antibactérienne contre les bactéries Gram-négatives et également contre les bactéries Gram-positives y compris le staphylocoque doré résistant à la méthiciline. Ces composés sont extrêmement utiles dans le traitement des maladies infectieuses.

  (EN) 新型头孢菌素衍生物，其制备方法，包括新型头孢菌素衍生物作为活性成分的预防和/或治疗传染病的组合物，以及头孢菌素衍生物合成中的中间化合物和其制备方法。本发明基于选择包含紧缩杂环环，特别是三唑嘧啶环或噻唑嘧啶环，作为头孢菌素骨架3位的取代基，以及包含儿茶酚基，特别是儿茶酚羧甲氧基亚胺基或儿茶酚羧基亚胺基，作为头孢菌素骨架7位的取代基。本发明中含有上述取代基的化合物对革兰氏阴性菌和包括甲氧西林耐药金黄色葡萄球菌在内的革兰氏阳性菌具有强大的抗菌活性。这些化合物在治疗传染病方面非常有用。 (FR) Nouveaux dérivés de céphalosporine, leurs procédés de préparation, compositions permettant de prévenir et/ou de traiter des maladies infectieuses et comportant les nouveaux dérivés de céphalosporine comme constituants actifs, ainsi que composés intermédiaires dans la synthèse des dérivés de céphalosporine et leurs procédés de préparation. La présente invention est fondée sur la sélection de groupes contenant un noyau hétérocyclique condensé, notamment un noyau de triazolopyrimidine ou un noyau de thiadiazolopyrimide, sous forme de substituants en position 3 du squelette de céphème, et de groupes contenant une fraction catéchol, en particulier une partie carboxyméthyloxyimino de catéchol ou une partie carboxymino de catéchol, sous forme de substituants en position 7 du squelette du céphème. Les composés ci-décrits contenant les substituants précités possèdent une forte activité antibactérienne contre les bactéries Gram-négatives et également contre les bactéries Gram-positives y compris le staphylocoque doré résistant à la méthiciline. Ces composés sont extrêmement utiles dans le traitement des maladies infectieuses.
• Intermediates cephalosporin derivatives
  申请人：Mochida Pharmaceutical Co., Ltd.

  公开号：US05064953A1

  公开（公告）日：1991-11-12

  The present invention relates to novel cephalosporin derivatives, processes for preparing thereof, compositions for preventing and/or treating infectious diseases which comprise the novel cephalosporin derivatives as active components, and the intermediate compounds in the synthesis of cephalosporin derivatives and processes for producing thereof. The novel cephalosporin derivatives according to the present invention contain condensed heterocyclic groups, particularly a triazolopyrimidine ring or a thiadiazolopyrimidine ring as substituents at the 3-position of the cephem skeleton, and a hydroxyimino, an alkyloxyimino or an acyloxyimino moiety as substituents at the 7-position of the cephem skeleton. The compounds of the present invention containing the aforementioned substituents have a strong antibacterial activity against gram-negative bacteria and also against gram-positive bacteria including methicillin-resistant Staphylococcus aureus. These compounds are extremely useful for the treatment of infectious diseases.

  本发明涉及新型头孢菌素衍生物，其制备方法，包含新型头孢菌素衍生物作为活性成分的预防和/或治疗传染病的组合物，以及头孢菌素衍生物合成中的中间体化合物和其制备方法。本发明中的新型头孢菌素衍生物含有紧凑的杂环基团，特别是三唑嘧啶环或噻唑嘧啶环作为头孢菌素骨架的3位取代基，并且羟肟基，烷氧肟基或酰氧肟基作为头孢菌素骨架的7位取代基。本发明中含有上述取代基的化合物对革兰氏阴性菌和包括甲氧西林耐药金黄色葡萄球菌在内的革兰氏阳性菌具有强烈的抗菌活性。这些化合物对于治疗传染病非常有用。
• Cephalosporin derivatives, processes for producing the same and compositions containing them
  申请人：MOCHIDA PHARMACEUTICAL CO., LTD.

  公开号：EP0150507A2

  公开（公告）日：1985-08-07

  Novel cephalosporin derivatives, processes for preparing thereof, compositions for preventing and/or treating infectious diseases which comprise the novel cephalosporin derivatives as active components, and the intermediate compounds in synthesis of cephalosporin derivative and processes for producing thereof are disclosed. The novel cephalosporin derivatives contain condensed heterocyclic groups, particularly a triazolopyrimidine ring or a thiadiazolopyrimidine ring as substituents at the 3-position of the cephem skeleton, and a hydroxyimino, an alkyloxyimino or an acyloxyimino moiety as substituents at the 7-position of the cephem skeleton. These compounds have a strong antibacterial activity against gram-negative bacteria and also against gram-positive bacteria including methicillin-resistant Staphylococcus aureus. They are extremely useful for the treatment of infectious diseases.

  本发明公开了新型头孢菌素衍生物、其制备工艺、包含新型头孢菌素衍生物作为活性成分的预防和/或治疗传染病的组合物，以及合成头孢菌素衍生物的中间化合物及其生产工艺。 新型头孢菌素衍生物含有缩合杂环基团，特别是在头孢骨架的 3 位上含有三唑嘧啶环或噻二唑嘧啶环作为取代基，在头孢骨架的 7 位上含有羟基亚氨基、烷氧基亚氨基或酰氧基亚氨基作为取代基。 这些化合物对革兰氏阴性菌和革兰氏阳性菌（包括耐甲氧西林金黄色葡萄球菌）具有很强的抗菌活性。它们对治疗传染病非常有用。