5-methanesulfonyloxymethyl-4-methyl-1,2,3-thiadiazole | 163008-87-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 5-methanesulfonyloxymethyl-4-methyl-1,2,3-thiadiazole
• 英文别名: 5-methanesulfonyloxymethyl-4-methyl-1,2,3-thiadiazol；(4-methylthiadiazol-5-yl)methyl methanesulfonate
• CAS: 163008-87-5
• 化学式: C₅H₈N₂O₃S₂
• 分子量: 208.262
• InChiKey: IDZUOLBVDVSRFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  硫代苯甲酸 、 5-methanesulfonyloxymethyl-4-methyl-1,2,3-thiadiazole 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以64%的产率得到5-benzoylthiomethyl-4-methyl-1,2,3-thiadiazole
  参考文献：
  名称：

  Orally active cephalosporins. Part 3: synthesis, structure–activity relationships and oral absorption of novel C-3 heteroarylmethylthio cephalosporins

  摘要：

  A series of 7 beta-[(Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-(heteroarylmethylthio)cephalosporins was designed, synthesized and evaluated for antibacterial activity and oral absorption in rats. Antibacterial activity was markedly influenced by the structure of the heteroaromatic ring moiety. Oral absorption was influenced by the heteroaromatic ring moiety as well as by the arrangement of heteroatoms. Among these compounds, FK041 (2o). having a 4-pyrazolylmethylthio moiety, showed potent antibacterial activity against both Gram-positive and Gram-negative bacteria including Haemophilus influenzae. Further, it showed higher oral absorption than CFDN. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00266-2
• 作为产物：
  描述：

  甲基磺酰氯 、 4-甲基-1,2,3-噻二唑-5-甲醇 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以98%的产率得到5-methanesulfonyloxymethyl-4-methyl-1,2,3-thiadiazole
  参考文献：
  名称：

  Orally active cephalosporins. Part 3: synthesis, structure–activity relationships and oral absorption of novel C-3 heteroarylmethylthio cephalosporins

  摘要：

  A series of 7 beta-[(Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-(heteroarylmethylthio)cephalosporins was designed, synthesized and evaluated for antibacterial activity and oral absorption in rats. Antibacterial activity was markedly influenced by the structure of the heteroaromatic ring moiety. Oral absorption was influenced by the heteroaromatic ring moiety as well as by the arrangement of heteroatoms. Among these compounds, FK041 (2o). having a 4-pyrazolylmethylthio moiety, showed potent antibacterial activity against both Gram-positive and Gram-negative bacteria including Haemophilus influenzae. Further, it showed higher oral absorption than CFDN. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00266-2

文献信息

• NOVEL CRYSTAL OF CEPHALOSPORIN COMPOUND
  申请人：——

  公开号：US20010007903A1

  公开（公告）日：2001-07-12

  A novel crystal of 7&bgr;-[2-(2-aminothiazol-4-yl)-2-(Z)-(hydroxyimino)acetamido]-3-[pyrazol-4-yl)methylthio]3-cephem-4-carboxylic acid or a salt thereof. Said compound is a cephalosporin antibiotic having very strong antibacterial activity which exhibits superior characteristics physically, chemically and pharmaceutically.

  一种7&bgr;-[2-(2-氨基噻唑-4-基)-2-(Z)-(羟亚胺)乙酰胺基]-3-[吡唑-4-基)甲硫基]头孢菌素-4-羧酸或其盐的新型晶体。该化合物是一种头孢菌素类抗生素，具有非常强的抗菌活性，具有优良的物理、化学和药学特性。
• Novel crystal of cephalosporin compound
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：US20010056089A1

  公开（公告）日：2001-12-27

  A novel crystal of 7&bgr;-[2-(2-aminothiazol-4-yl)-2-(Z)-(hydroxyimino)acetamido]-3-[pyrazol-4-yl)methylthio]3-cephem-4-carboxylic acid or a salt thereof. Said compound is a cephalosporin antibiotic having very strong antibacterial activity which exhibits superior characteristics physically, chemically and pharmaceutically.

  一种7β-[2-(2-氨基噻唑-4-基)-2-(Z)-(羟亚胺基)乙酰氨基]-3-[吡唑-4-基)甲硫基]3-头孢烯-4-羧酸或其盐的新型晶体。该化合物是一种头孢菌素类抗生素，具有非常强的抗菌活性，物理、化学和药学特性均表现出优越性。
• Cephem compounds
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US06468995B1

  公开（公告）日：2002-10-22

  A compound of the formula: wherein R1 is amino or protected amino; R2 is hydrogen, lower alkyl or hydroxy protective group; R3 is carboxy or protected carboxy; R4 is an unsubstituted 5, 6 or 7-membered heteromonocyclic group containing two nitrogen atoms as heteroatoms, and which optionally further contains one oxygen or sulfur atom; or R4 is said 5, 6 or 7-membered heteromonocyclic group substituted by 1 to 4 groups selected from the group consisting of lower alkyl, lower alkoxy, lower alkylthio, lower alkylamino, cyclo(lower)alkyl, cyclo(lower)alkenyl, halogen, amino, protected amino, protected hydroxy, cyano, nitro, carboxy, hydroxy(lower)alkyl, amino(lower)alkyl, and carbamoyloxy; and n is 1 or 2.

  该化合物的公式为：其中R1是氨基或保护氨基；R2是氢、低级烷基或羟基保护基；R3是羧基或保护羧基；R4是未取代的含有两个氮原子作为杂原子的5、6或7元杂单环族，可选地进一步含有一个氧或硫原子；或者R4是该5、6或7元杂单环族中的1至4个基团所取代，所述基团选自低级烷基、低级烷氧基、低级烷基硫基、低级烷基氨基、环(低级)烷基、环(低级)烯基、卤素、氨基、保护氨基、保护羟基、氰基、硝基、羧基、羟基(低级)烷基、氨基(低级)烷基和氨基甲酰氧基；n为1或2。
• Orally active cephalosporins. Part 3: synthesis, structure–activity relationships and oral absorption of novel C-3 heteroarylmethylthio cephalosporins
  作者：Hirofumi Yamamoto、Takeshi Terasawa、Ayako Nakamura、Kohji Kawabata、Hisashi Takasugi、Hirokazu Tanaka、Satoru Matsumoto、Yoshimi Matsumoto、Shuichi Tawara

  DOI：10.1016/s0968-0896(00)00266-2

  日期：2001.2

  A series of 7 beta-[(Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-(heteroarylmethylthio)cephalosporins was designed, synthesized and evaluated for antibacterial activity and oral absorption in rats. Antibacterial activity was markedly influenced by the structure of the heteroaromatic ring moiety. Oral absorption was influenced by the heteroaromatic ring moiety as well as by the arrangement of heteroatoms. Among these compounds, FK041 (2o). having a 4-pyrazolylmethylthio moiety, showed potent antibacterial activity against both Gram-positive and Gram-negative bacteria including Haemophilus influenzae. Further, it showed higher oral absorption than CFDN. (C) 2001 Elsevier Science Ltd. All rights reserved.