cephalothin tert-butyl ester | 55151-60-5

• 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: cephalothin tert-butyl ester
• 英文别名: (6R)-3-acetoxymethyl-8-oxo-7t-(2-thiophen-2-yl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester；7β-(2-thiophen-2-yl-acetylamino)-cephalosporanic acid tert-butyl ester；t-butyl 7-(2-thienylacetamido)cephalosporanate；tert-butyl (6R,7R)-3-(acetyloxymethyl)-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 55151-60-5
• 化学式: C₂₀H₂₄N₂O₆S₂
• 分子量: 452.552
• InChiKey: JNMXRZLTEMBYQV-CRAIPNDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  156
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  cephalothin tert-butyl ester 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以64%的产率得到(6R,7R)-3-Acetoxymethyl-5,5,8-trioxo-7-(2-thiophen-2-yl-acetylamino)-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Inhibition of human leukocyte elastase. 1. Inhibition by C-7-substituted cephalosporin tert-butyl esters

  摘要：

  Time-dependent inhibitors of the enzyme human leukocyte elastase have been developed based on the cephem nucleus. A series of cephalosporin tert-butyl esters has been examined, and the activity of these compounds has been found to be very sensitive to C-7 substituents, with small, alpha-oriented, electron-withdrawing groups showing greatest activity. Additionally, the oxidation state of the sulfur atom has been found to play a role in potency, with sulfones showing considerably greater activity than the corresponding sulfides or beta-sulfoxides. The alpha-sulfoxides were inactive.

  DOI：

  10.1021/jm00171a028
• 作为产物：
  描述：

  (6R)-3-acetoxymethyl-7t-(2-carboxy-benzoylamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester 在 N,N'-二环己基碳二亚胺 作用下， 反应 2.0h， 生成 cephalothin tert-butyl ester
  参考文献：
  名称：

  来信：氮杂环丁酮抗生素。十四。从酸和碱敏感化合物中除去邻苯二甲酰基保护基。

  摘要：

  DOI：

  10.1021/ja00852a044

文献信息

• Progress towards a stable cephalosporin-halogenated phenazine conjugate for antibacterial prodrug applications
  作者：Tao Xiao、Ke Liu、Robert W. Huigens

  DOI：10.1016/j.bmcl.2020.127515

  日期：2020.11

  conventional antibiotic therapies during infection, often leading to significant illness and death. Our lab has discovered halogenated phenazine (HP) analogues which demonstrate potent antibacterial activities through a unique iron-starving mechanism. Herein, we describe synthetic efforts towards a stable cephalosporin-HP conjugate prodrug with the aim of translating HPs into useful clinical agents. Ceph

  耐药细菌在感染期间成功地逃避了常规抗生素疗法的作用，通常会导致严重的疾病和死亡。我们的实验室发现了卤化吩嗪 (HP) 类似物，它们通过独特的缺铁机制显示出强大的抗菌活性。在此，我们描述了针对稳定的头孢菌素-HP 缀合物前药的合成努力，目的是将 HP 转化为有用的临床药物。头孢菌素-抗生素偶联物为抗菌设计提供了多种优势，包括在 β-内酰胺弹头选择性开环后通过靶向细胞内头孢菌素酶释放活性剂。在这些研究中，碳酸盐连接的头孢菌素-HP 偶联物16被合成；然而，我们无法成功去除头孢菌素酶加工所需的酯基。然后将头孢菌素-HP 16用作探针来研究碳酸盐接头在抗菌试验中的稳定性，正如预测的那样，该化合物被证明对金黄色葡萄球菌无活性（MIC > 100 µM）。缺乏16的抗菌活性可归因于碳酸盐接头在整个 MIC 测定中保持完整，因此不会释放活性 HP 部分。与我们之前报道的高度不稳定的醚连接类似物相比，这些
• Process for preparing 3-iodomethyl cephalosporins
  申请人：ELI LILLY AND COMPANY

  公开号：EP0034924A2

  公开（公告）日：1981-09-02

  A process is described for preparing a 3-iodomethyl cephalosporin of the formula which comprisesreacting in an aprotic solvent under substantially anhydrous conditions at a temperature between about 0°C and about 35°C a 3-alkanoylmethyl or 3-carbamoyloxymethyl cephalosporin oftheformula with a trialkylsilyl iodide of the formula where in the above formulas R is the residue of a carboxylic acid as defined in the specification; Ro is hydrogen or methoxy; R1 is C1-C4 alkyl, 2,2,2-trichloroethyl, iodomethyl, diphenylmethyl, benzyl, substituted benzyl substituted by methyl, methoxy or nitro; or R is a trialkylsilyl group of the formula wherein R3, R3, and R-3; are independentlyC1-C3alkyl; orR1 is sodium or potassium; R'1 has the same meanings as R1, provided that, when R is sodium, potasstum. diphenylmethyl, or p-methoxybenzyl, R'1 is R2 is C1-C4 alkanoyloxy or a carbamoyloxy group of the formula wherein R'2 and R"2 are independently hydrogen or C1-C3 alkyl; and nis 0 or 1; with the limitation that when n is 1, the double bond represented by the dotted bonding lines is in the 3-position. The 3-iodomethyl cephalosporins are useful intermediates for antibiotics.

  一种制备式 3-碘甲基头孢菌素的工艺包括 其中包括在基本无水的条件下，在约 0°C 至约 35°C 的温度下，在无水溶剂中将式中的 3-烷酰甲基或 3-氨基甲酰氧甲基头孢菌素与式中的三烷基硅碘化物反应 与式中的三烷基硅烷基碘化物反应 在上述公式中，R 是说明书中定义的羧酸残基； Ro 是氢或甲氧基； R1 是 C1-C4 烷基、2,2,2-三氯乙基、碘甲基、二苯甲基、苄基、被甲基、甲氧基或硝基取代的取代苄基；或 R 是式中的三烷基硅基 其中 R3、R3 和 R-3 独立地为 C1-C3 烷基；或 R1 为钠或钾； R'1 的含义与 R1 相同，但当 R 是钠、钾、二苯甲基或对甲氧基苄基时，R'1 是 R2 是式中的 C1-C4 烷酰氧基或氨基甲酰氧基。 其中 R'2 和 R "2 独立地为氢或 C1-C3 烷基；以及 n 为 0 或 1； 但当 n 为 1 时，虚线所代表的双键位于 3 位。3-iodomethyl cephalosporins 是抗生素的有用中间体。
• CYTOTOXIC COMPOUNDS
  申请人：Medarex, Inc.

  公开号：EP1948242B1

  公开（公告）日：2011-09-14
• Cytotoxic Compounds and Conjugates
  申请人：Gangwar Sanjeev

  公开号：US20080293800A1

  公开（公告）日：2008-11-27

  The present disclosure provides cytoxic compounds useful as drugs or prodrugs and to drug-cleavable substrate conjugates where the drug and cleavable substrate are optionally linked through a self-immolative linker.
• US4159372A
  申请人：——

  公开号：US4159372A

  公开（公告）日：1979-06-26