7-Aminocephalosporanic acid t-butyl ester | 6187-87-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 7-Aminocephalosporanic acid t-butyl ester
• 英文别名: 3-Acetoxymethyl-7-amino-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester；tert-butyl (6R,7R)-3-(acetyloxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 6187-87-7
• 化学式: C₁₄H₂₀N₂O₅S
• 分子量: 328.389
• InChiKey: SKVHPNQACYIQDC-BXKDBHETSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  124
• 氢给体数：
  1
• 氢受体数：
  7

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  7-氨基头孢烷酸	7-Aminocephalosporanic acid	957-68-6	C10H12N2O5S	272.282

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	tert-butyl 3-(acetoxymethyl)-7α-formamido-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate	127733-16-8	C15H20N2O6S	356.4
  ——	tert-butyl 7α-<(methoxycarbonyl)amino>-3-(acetoxymethyl)-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate	102253-57-6	C16H22N2O7S	386.426
  ——	tert-butyl (6R,7R)-3-(acetoxymethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	53638-83-8	C22H26N2O6S	446.524
  ——	cephalothin tert-butyl ester	55151-60-5	C20H24N2O6S2	452.552
  ——	tert-butyl 3-(acetoxymethyl)-7α-<(2-thienyl)acetamido>-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate	127733-15-7	C20H24N2O6S2	452.552
  ——	(6R)-3-acetoxymethyl-7c-hydroxy-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester	63599-58-6	C14H19NO6S	329.374
  ——	7-Trifluoromethylsulfonylacetamidocephalosporin	51244-97-4	C13H13F3N2O8S2	446.382
  ——	t-butyl 3-acetoxymethyl-7α-methoxy-3-cephem-4-carboxylate	95570-83-5	C15H21NO6S	343.401
  ——	(6R,7S)-3-Acetoxymethyl-8-oxo-7-propyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester	127733-06-6	C17H25NO5S	355.455
  ——	3-Acetoxymethyl-8-oxo-7-propoxy-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester	127732-88-1	C17H25NO6S	371.455

反应信息

• 作为反应物：
  描述：

  7-Aminocephalosporanic acid t-butyl ester 生成 (6R)-3-acetoxymethyl-7t-((R)-2-benzo[1,3]dioxol-5-yl-2-hydroxy-acetylamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid; triethylamine salt
  参考文献：
  名称：

  半合成头孢菌素。7-mandelamido-3-cephem-4-羧酸的合成及其构效关系。

  摘要：

  DOI：

  10.1021/jm00247a008
• 作为产物：
  描述：

  (6R)-3-acetoxymethyl-8-oxo-7t-(3-oxo-3H-isobenzofuran-1-ylideneamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester 在 肼 作用下， 以 四氢呋喃 为溶剂， 生成 7-Aminocephalosporanic acid t-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

• Use of src SH2 specific compounds to treat a bone resorption disease
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP0727211A1

  公开（公告）日：1996-08-21

  Invented is a method of treating a bone resorption disease in a subject which comprises administering to the subject a therapeutically effective amount of a compound which binds to a human src SH2 domain with a binding affinity greater than fifty-fold higher than the binding affinity with which the compound binds to a human lck SH2 domain and a human fyn SH2 domain, and, binds to a human hcp SH2 domain, a human Grb2 SH2 domain, a human SH-PTP2 SH2 domain and a human p85 SH2 domain with a binding affinity which is greater than fifty-fold lower than the binding affinity with which the compound binds to such src SH2 domain.

  已发明一种治疗骨吸收疾病的方法，包括向受试者施用与人src SH2结构域结合的化合物的治疗有效量，其结合亲和力比其与人lck SH2结构域和人fyn SH2结构域结合的结合亲和力高出五十倍以上，并且与人hcp SH2结构域、人Grb2 SH2结构域、人SH-PTP2 SH2结构域和人p85 SH2结构域结合的结合亲和力比其与该src SH2结构域结合的结合亲和力低五十倍以上。
• Palladium Catalysed Tandem Cyclisation–Anion Capture. Part 6: Synthesis of Sugar, Nucleoside, Purine, Benzodiazepinone and β-lactam Analogues via Capture of in situ Generated Vinylstannanes
  作者：Adele Casaschi、Ronald Grigg、José M. Sansano

  DOI：10.1016/s0040-4020(00)00661-x

  日期：2000.9

  The regioselective palladium catalysed hydrostannylation of alkynes bearing a β-heteroatom affords mainly α-vinyltin(IV) compounds that are used as terminating species in palladium catalysed cyclisation–anion capture processes. The pharmacophore attached to the alkyne moiety permits the synthesis of sugars, nucleosides, purines, benzodiazepinones and β-lactams analogues in good yields.

  带有β-杂原子的炔烃的区域选择性钯催化的氢化锡烷基化主要提供α-乙烯基锡（IV）化合物，这些化合物在钯催化的环化-阴离子捕获过程中用作终止物种。附于炔部分的药效基团允许以高收率合成糖，核苷，嘌呤，苯并二氮杂酮和β-内酰胺类似物。
• Thiazolylacetamido cephalosporin type compounds
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04098888A1

  公开（公告）日：1978-07-04

  Novel cephem compounds of the formula; ##STR1## wherein R.sup.1 represents amino or hydroxyl group which may be protected, R.sup.2 represents amino or hydroxyl group or a group convertible into these groups, R.sup.3 represents hydrogen or methoxy group or a group convertible into methoxy group, R.sup.4 represents hydrogen or a residue of a nucleophilic compound and R.sup.8 represents hydrogen or a halogen, or a pharmaceutically acceptable salt or ester thereof, have strong antibiotic properties against a wide variety of microorganisms including gram-positive bacteria as well as gram-negative ones, especially by oral administration and can be used as therapeutic agent for various bacterial infections of animals including human beings.

  新型头孢菌素化合物的化学式如下；##STR1## 其中R.sup.1代表氨基或羟基，可以被保护，R.sup.2代表氨基或羟基或可转化为这些基团的基团，R.sup.3代表氢或甲氧基或可转化为甲氧基的基团，R.sup.4代表氢或亲核化合物的残基，R.sup.8代表氢或卤素，或其药用可接受的盐或酯，具有强大的抗生素特性，对包括革兰氏阳性细菌和革兰氏阴性细菌在内的各种微生物具有抗性，特别是经口服给药，可用作动物包括人类的各种细菌感染的治疗剂。
• 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
• Synthesis and evaluation of novel β-lactam inhibitors of human leukocyte elastase
  作者：K P Koteva、André M Cantin、W A Neugebauer、E Escher

  DOI：10.1139/v01-062

  日期：2001.4.1

  and tissue diseases. The most potent IC50 values were obtained with neutral hydrophobic 7α-methoxy cephalosporanic acid derivatives. Tryptophanyl-9-fluorenylmethyl ester and N-benzhydryl piperazine derivatives of 7α-methoxy cephalosporanic acid represent two novel HLE inhibitors, with length of action persisting beyond 24 h.

  合成并测试了一系列 β-内酰胺衍生物，以确定抑制人类白细胞弹性蛋白酶 (HLE) 的构效关系，HLE 是一种参与多种退行性肺和组织疾病的丝氨酸蛋白酶。使用中性疏水性 7α-甲氧基头孢烷酸衍生物获得最有效的 IC50 值。7α-甲氧基头孢烷酸的色氨酸-9-芴基甲酯和 N-二苯甲基哌嗪衍生物是两种新型 HLE 抑制剂，作用持续时间超过 24 小时。