4-benzoylthiomethyl-1-(trityl)pyrazole | 163008-91-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 4-benzoylthiomethyl-1-(trityl)pyrazole
• 英文别名: 4-benzoylthiomethyl-1-tritylpyrazole；S-[(1-tritylpyrazol-4-yl)methyl] benzenecarbothioate
• CAS: 163008-91-1
• 化学式: C₃₀H₂₄N₂OS
• 分子量: 460.599
• InChiKey: FINXBEFKPZCPIJ-UHFFFAOYSA-N

物化性质

• 沸点：
  630.5±55.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  60.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7β-acylcephem 、 4-benzoylthiomethyl-1-(trityl)pyrazole 在 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 以93%的产率得到Δ³ cephem
  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：

  (1-三苯甲基-1H-吡唑-4-基)甲醇 以66的产率得到4-benzoylthiomethyl-1-(trityl)pyrazole
  参考文献：
  名称：

  Journal of Antibiotics. 1998, 51, 683-687

  摘要：

  DOI：
• 作为试剂：
  描述：

  7β-acylcephem 、 4-benzoylthiomethyl-1-(trityl)pyrazole 在 4-benzoylthiomethyl-1-(trityl)pyrazole 作用下， 以94的产率得到Δ³ cephem
  参考文献：
  名称：

  Journal of Antibiotics. 1998, 51, 683-687

  摘要：

  DOI：

文献信息

• [EN] NEW CEPHEM COMPOUNDS<br/>[FR] NOUVEAUX COMPOSES DE CEPHEME
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：WO1995007283A1

  公开（公告）日：1995-03-16

  (EN) New cephem compounds of formula (I), wherein R1 is amino or protected amino, R2 is hydrogen, lower alkyl or hydroxy protective group, R3 is carboxy or protected carboxy, R4 is 3-pyridyl, 4-pyridyl or optionally substituted heteromonocyclic group containing two nitrogen atoms as hetero atoms, and which may also contain one oxygen or sulfur atom, and n is 0, 1 or 2, provided that when R2 is lower alkyl, then n is 1 or 2 and R4 is optionally substituted heteromonocyclic group containing two nitrogen atoms as hetero atoms, and which may also contain one oxygen or sulfur atom, and pharmaceutically acceptable salts thereof which are useful as a medicament.(FR) L'invention porte sur des nouveaux composés céphème représentés par la formule suivante: (I) dans laquelle R1 représente amino ou amino protégé, R2 représente hydrogène, alkyle inférieur ou un groupe protecteur hydroxy, R3 représente carboxy ou carboxy protégé, R4 représente 3-pyridyle, 4-pyridyle ou un groupe hétéromonocyclique éventuellement substitué contenant deux atomes d'azote en tant qu'hétéroatomes et pouvant également contenir un atome d'oxygène ou de soufre, et n correspond à 0, 1 ou 2, à condition que, lorsque R2 représente alkyle inférieur, n corresponde à 1 ou 2, et R4 représente un groupe hétéromonocyclique contenant deux atomes d'azote en tant qu'hétéroatomes et pouvant également contenir un atome d'oxygène ou de soufre. L'invention se rapporte également à des sels pharmaceutiquement acceptables desdits composés pouvant être utilisés en tant que médicament.

  新的头孢菌素化合物的化学式为（I），其中R1为氨基或保护的氨基，R2为氢、低碳基或羟基保护基，R3为羧基或保护的羧基，R4为3-吡啶基、4-吡啶基或可选取代的含有两个氮原子作为杂原子的杂单环族基，且可能还包含一个氧或硫原子，n为0、1或2，但当R2为低碳基时，n为1或2，且R4为可选取代的含有两个氮原子作为杂原子的杂单环族基，且可能还包含一个氧或硫原子。这些化合物的药物可接受的盐可用作药物。
• 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。
• FK041, a Novel Orally Active Cephalosporin: Synthesis and Biological Properties.
  作者：HIROFUMI YAMAMOTO、KOHJI KAWABATA、SHUICHI TAWARA、HISASHI TAKASUGI、HIROKAZU TANAKA

  DOI：10.7164/antibiotics.51.683

  日期：——
• Orally Active Cephalosporins. Part 4: Synthesis, Structure–Activity Relationships and Oral Absorption of Novel 3-(4-Pyrazolylmethylthio)cephalosporins with Various C-7 Side Chains
  作者：Hirofumi Yamamoto、Yoshiteru Eikyu、Shinya Okuda、Kohji Kawabata、Hisashi Takasugi、Hirokazu Tanaka、Satoru Matsumoto、Yoshimi Matsumoto、Shuichi Tawara

  DOI：10.1016/s0968-0896(01)00416-3

  日期：2002.5

  A series of 3-(4-pyrazolylmethylthio)cephalosporins with various C-7 side chains was designed, synthesized and evaluated for antibacterial activity and oral absorption in rats. Antibacterial activity against Haemophilus influenzae was markedly increased by the C-7 oxime moiety. Deamination at the 2 position of, or introduction of a substituent such as halogen or methyl to, the 5 position of the (Z)-2-(2-aminothiazol-4-yl)-2-(hydroxyimino) moiety improved oral absorption. Among these compounds, FR192752 (40a) having a (Z)-2-(2-amino-5-chlorothiazol-4-yl)-2-hydroxyiminoacetam do moiety, showed potent antibacterial activity against both Gram-positive and Gram-negative bacteria including H. influenzae and penicillin G-resistant Streptococcus pneumoniae (PRSP). Further, it showed higher oral absorption than CFDN and FK041. (C) 2002 Elsevier Science Ltd, All rights reserved.