benzhydryl 7β-(2-thienylacetamido)-3-(chloromethyl)-3-cephem-4-carboxylate | 26748-89-0

• 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: benzhydryl 7β-(2-thienylacetamido)-3-(chloromethyl)-3-cephem-4-carboxylate
• 英文别名: (6R,7R)-benzhydryl 3-(chloromethyl)-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate；Diphenylmethyl 3-chloromethyl-7beta-(2'thienylacetamido)-ceph-3-em-4-carboxylate；benzhydryl (6R,7R)-3-(chloromethyl)-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 26748-89-0
• 化学式: C₂₇H₂₃ClN₂O₄S₂
• 分子量: 539.076
• InChiKey: YHMWMVYUTQFAFS-ATIYNZHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  129
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzhydryl 7β-(2-thienylacetamido)-3-(chloromethyl)-3-cephem-4-carboxylate 在 sodium hydroxide 、 三氟乙酸 、 sodium iodide 作用下， 以 二氯甲烷 、 乙酸乙酯 、 苯甲醚 、 丙酮 为溶剂， 反应 3.17h， 生成 (5S,6R,7R)-5,8-Dioxo-3-[(Z)-3-(7-oxo-7H-phenoxazin-3-yloxy)-propenyl]-7-(2-thiophen-2-yl-acetylamino)-5λ4-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  用于成像 β-内酰胺酶基因表达的新型荧光底物

  摘要：

  一类新的小型无荧光荧光底物在 β-内酰胺酶水解后发出明亮的荧光，荧光强度提高了 153 倍。细胞裂解物中低于 500 fM 的 β-内酰胺酶可以很容易地检测到，并且活细胞中的 β-内酰胺酶表达可以用红色荧光衍生物成像。这些新的荧光底物应可用于临床诊断并促进 β-内酰胺酶作为生物传感器的应用。

  DOI：

  10.1021/ja036126o
• 作为产物：
  描述：

  diphenylmethyl 7β-(2-thienylacetamido)-3-(hydroxymethyl)-cephem-4-carboxylate 在 吡啶 、 三光气 作用下， 以 四氢呋喃 为溶剂， 以60%的产率得到benzhydryl 7β-(2-thienylacetamido)-3-(chloromethyl)-3-cephem-4-carboxylate
  参考文献：
  名称：

  Facile chloride substitution of activated alcohols by triphosgene: application to cephalosporin chemistry

  摘要：

  DOI：

  10.1021/jo00025a046

文献信息

• Synthesis of cephalosporin-3′-diazeniumdiolates: biofilm dispersing NO-donor prodrugs activated by β-lactamase
  作者：Nageshwar Rao Yepuri、Nicolas Barraud、Nasim Shah Mohammadi、Bharat G. Kardak、Staffan Kjelleberg、Scott A. Rice、Michael J. Kelso

  DOI：10.1039/c3cc40869h

  日期：——

  Use of biofilm dispersing NO-donor compounds in combination with antibiotics has emerged as a promising new strategy for treating drug-resistant bacterial biofilm infections. This paper details the synthesis and preliminary evaluation of six cephalosporin-3'-diazeniumdiolates as biofilm-targeted NO-donor prodrugs. Each of the compounds is shown to selectively release NO following reaction with the

  生物膜分散NO供体化合物与抗生素的结合使用已成为治疗耐药细菌生物膜感染的有前途的新策略。本文详细介绍了六种头孢菌素3'-二氮杂二醇盐作为生物膜靶向NO供体前药的合成和初步评估。已显示每种化合物在与细菌特异性酶β-内酰胺酶反应后选择性释放NO，并在体外触发铜绿假单胞菌生物膜的分散。
• Cephalosporin compounds
  申请人：Glaxo Laboratories Limited

  公开号：US03948906A1

  公开（公告）日：1976-04-06

  7.beta.-Amino- and acylamidoceph-3-em-4-carboxylic acids having at the 3-position a halo-, formyloxy-, isothiocyanato- or haloacetoxymethyl group and salts and esters thereof. These compounds are useful as starting compounds for preparing 7.alpha.-acylamidoceph-3-em-4-carboxylic acids having a group at the 3-position, other than 3-acetoxymethyl, by reaction with a nucleophile. The compounds prepared have modified antibiotic activity.

  7.beta.-氨基和酰胺基头孢-3-乙烯-4-羧酸，在3位具有卤素、甲氧基甲酰氧基、异硫氰酸酯或卤代乙酰氧甲基基团和其盐和酯。这些化合物可用作制备具有3位上除3-乙酰氧甲基外其他基团的7.alpha.-酰胺基头孢-3-乙烯-4-羧酸的起始化合物，通过与亲核试剂反应。制备的化合物具有改性的抗生素活性。
• Novel fluorogenic substrates for beta-lactamase gene expression
  申请人：Tsien Y. Roger

  公开号：US20070020715A1

  公开（公告）日：2007-01-25

  Provided are fluorescent substrates β-lactamases and methods of using substrates having the general formulas: or in which where R 1 is H or A is S, O, SO, SO 2 or CH 2 ; X is O; L is a linker; R 2 is hydrogen; R 3 is hydrogen; R 4 is hydrogen; R 5 is hydrogen; R 6 is hydrogen; R 7 is hydrogen; R 8 is hydrogen; R 9 is in which W is a hydrogen, alkyl, substituted heteroalkyl, aryl, a heteroaryl, substituted heteroaryl or a CN; and, S is an integer from 0 to 5; W′ and W″ are independently hydrogen, alkyl, substituted heteroalkyl, aryl, substituted heteroaryl, (═O) or OR 10 ; wherein R 10 is hydrogen, substituted alkyl, heteroalkyl, substituted heteroalkyl, aryl, substituted aryl, heteroaryl; or substituted heteroaryl; and, Y is a dye moiety or a quencher moiety. R is a benzyl, 2-thienylmethyl, or cyanomethyl group; R′ is selected from the group consisting of H, physiologically acceptable salts or metal, ester groups, ammonium cations, —CHR 2 OCO(CH 2 ) n CH 3 , —CHR 2 OCOC(CH 3 ) 3 , acylthiomethyl, acyloxy-alpha-benzyl, deltabutyrolactonyl, methoxycarbonyloxymethyl, phenyl, methylsulphinylmethyl, β-morpholinoethyl, dialkylaminoethyl, and dialkylaminocarbonyloxymethyl, in which R 2 is selected from the group consisting of H and lower alkyl; A is selected from the group consisting of S, O, SO, SO 2 and CH 2 ; and Z is a donor fluorescent moiety. Also provided are methods of use of the compounds of the general formulas.
• US7427680B2
  申请人：——

  公开号：US7427680B2

  公开（公告）日：2008-09-23
• US7396926B2
  申请人：——

  公开号：US7396926B2

  公开（公告）日：2008-07-08