(R)-7-<(3-benzothienyl)glycylamido>-3-methyl-3-cephem-4-carboxylic acid | 92218-37-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (R)-7-<(3-benzothienyl)glycylamido>-3-methyl-3-cephem-4-carboxylic acid
• 英文别名: (R)-7-(3-benzothienylglycylamido)-3-methyl-3-cephem-4-carboxylic acid；(R)-7-(3-benzothienylglycylamido)deacetoxycephalosporanic acid；7-((Aminobenzo(b)thien-3-ylacetyl)amino)-3-methyl-3-cephem-4-carboxylic acid；(6R,7R)-7-[[(2R)-2-amino-2-(1-benzothiophen-3-yl)acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS: 92218-37-6
• 化学式: C₁₈H₁₇N₃O₄S₂
• 分子量: 403.483
• InChiKey: UZIXWKQHCIOPLV-PBFPGSCMSA-N

物化性质

• 沸点：
  804.3±65.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  166
• 氢给体数：
  3
• 氢受体数：
  7

制备方法与用途

LY164846是一种新型口服头孢菌素，对葡萄球菌、链球菌、流感嗜血杆菌、卡他莫拉氏菌和奈瑟菌具有良好的抗菌效果。

反应信息

• 作为产物：
  描述：

  alpha-<(3-methoxy-1-methyl-3-oxo-1-propenyl)amino>benzothiophene-3-acetic acid sodium salt 在 N,N-二甲基苄胺 作用下， 反应 6.0h， 生成 (R)-7-<(3-benzothienyl)glycylamido>-3-methyl-3-cephem-4-carboxylic acid
  参考文献：
  名称：

  Balogh, Douglas W.; Patterson, Lawrence E.; Wheeler, William J, Synthetic Communications, 1988, vol. 18, # 3, p. 307 - 312

  摘要：

  DOI：

文献信息

• Orally absorbable cephalosporin antibiotics. 3. Preparation of biologically active R-isomer of 7-(3-benzothienylglycylamido)deacetoxycephalosporanic acid
  作者：Stjepan Kukolja、Janice L. Pfeil、Susan E. Draheim、John L. Ott

  DOI：10.1021/jm00150a024

  日期：1985.12

  were resolved with (+)- and (-)-tartaric acid in acetonitrile to give the corresponding R and S salts. The R-salt 4 was hydrolyzed to (R)-3-benzothienylglycine (5). The amino group in 5 was protected with the Boc function and the protected R amino acid 6 coupled with the p-NB ester of 7-ADCA to give the diprotected cephalosporin 7. After removal of the Boc and p-NB groups, the R isomer of 7-(3-benzo

  将（RS）-3-苯并噻吩基甘氨酸的甲基和异丙基酯用（+）-和（-）-酒石酸在乙腈中拆分，得到相应的R和S盐。R盐4水解为（R）-3-苯并噻吩基甘氨酸（5）。5中的氨基被Boc功能保护，被保护的R氨基酸6与7-ADCA的p-NB酯偶联，得到双保护的头孢菌素7。除去Boc和p-NB基团后，R异构体获得了7-（3-苯并噻吩基糖基氨基）脱乙酰氧基头孢菌酸（1）。通过制备色谱将差向性头孢菌素7的p-NB酯分离为R和S异构体。除去保护基后，分离出S差向异构体。报道了R和S差向异构体与头孢菌素1的RS混合物的抗菌活性的比较。
• Orally absorbable cephalosporin antibiotics. 1. Structure-activity relationships of benzothienyl- and naphthylglycine derivatives of 7-aminodeacetoxycephalosporanic acid
  作者：Stjepan Kukolja、Susan E. Draheim、Janice L. Pfeil、Robin D. G. Cooper、Bernard J. Graves、Richard E. Holmes、David A. Neel、George W. Huffman、J. Alan Webber

  DOI：10.1021/jm00150a022

  日期：1985.12

  A structure-activity relationship study of a number of orally absorbed cephalosporins together with their syntheses is described. These new cephalosporins are benzothienyl- and naphthylglycine derivatives of 7-aminodeacetoxycephalosporanic acid. Several different synthetic methods for the glycine side chains, their protection, and the final acylations are reported. Several of these analogues were more active than cephalexin both in vitro and in vivo against commonly encountered Gram-positive bacteria. (R)-7-(3-Benzothienylglycylamido)-3-methyl-3-cephem-4-carboxylic acid (1R) has emerged as a potent antibacterial agent and is currently undergoing preclinical evaluation.
• BOLOGH, DOUGLAS W.;PATTERSON, LAWRENCE E.;WHEELER, WILLIAM J., SUNTH. COMMUN., 18,(1988) N 3, 307-312
  作者：BOLOGH, DOUGLAS W.、PATTERSON, LAWRENCE E.、WHEELER, WILLIAM J.

  DOI：——

  日期：——
• Balogh, Douglas W.; Patterson, Lawrence E.; Wheeler, William J, Synthetic Communications, 1988, vol. 18, # 3, p. 307 - 312
  作者：Balogh, Douglas W.、Patterson, Lawrence E.、Wheeler, William J

  DOI：——

  日期：——