allyl 7β-(2-(thien-2-yl)acetamido)-3-(acetoxymethyl)-3-cephem-4-carboxylate | 104949-45-3

• 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: allyl 7β-(2-(thien-2-yl)acetamido)-3-(acetoxymethyl)-3-cephem-4-carboxylate
• 英文别名: allyl 7β-(2-thienylacetamido)-3-(acetoxymethyl)-3-cephem-4-carboxylate；prop-2-enyl (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: 104949-45-3
• 化学式: C₁₉H₂₀N₂O₆S₂
• 分子量: 436.51
• InChiKey: UAQPJNMWGHDPNW-CRAIPNDOSA-N

物化性质

• 沸点：
  712.7±60.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 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：

  allyl 7β-(2-(thien-2-yl)acetamido)-3-(acetoxymethyl)-3-cephem-4-carboxylate 在 碘代三甲硅烷 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of beta-Lactamase activated nitric oxide donors

  摘要：

  In order to achieve site specific delivery of NO, we designed conjugates of cephalosporin with NO donors. NO donors such as cupferron and SIN-1 were evaluated as potential choices for conjugates. Cephalosporin conjugated with SIN-1 demonstrated promising beta-lactamase dependent NO releasing ability. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00242-7
• 作为产物：
  描述：

  sodium cephalothin 、 3-溴丙烯 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以41%的产率得到allyl 7β-(2-(thien-2-yl)acetamido)-3-(acetoxymethyl)-3-cephem-4-carboxylate
  参考文献：
  名称：

  COMPOSITIONS AND METHODS FOR ADOPTIVE CELL THERAPY FOR CANCER

  摘要：

  本文提供了一种包括表达肿瘤抗原靶向嵌合抗原受体和一种前药转化酶的工程免疫细胞的细胞治疗组合物和方法。

  公开号：

  US20200215111A1

文献信息

• [EN] COMPOSITIONS AND METHODS FOR ADOPTIVE CELL THERAPY<br/>[FR] COMPOSITIONS ET PROCÉDÉS POUR LA THÉRAPIE CELLULAIRE ADOPTIVE
  申请人：MEMORIAL SLOAN KETTERING CANCER CENTER

  公开号：WO2019006467A1

  公开（公告）日：2019-01-03

  Provided herein are compositions and methods for adoptive cell therapy comprising engineered immune cells that express an antigen-targeted chimeric antigen receptor and a prodrug converting enzyme for the treatment of inflammation, inflammatory diseases, or pathogenic infections.

  本文提供了一种采用工程免疫细胞的细胞治疗组合物和方法，这些免疫细胞表达靶向抗原的嵌合抗原受体和一种前药转化酶，用于治疗炎症、炎症性疾病或病原体感染。
• [EN] COMPOSITIONS AND METHODS FOR ADOPTIVE CELL THERAPY FOR CANCER<br/>[FR] COMPOSITIONS ET MÉTHODES DE THÉRAPIE CELLULAIRE ADOPTIVE CONTRE LE CANCER
  申请人：MEMORIAL SLOAN KETTERING CANCER CENTER

  公开号：WO2019006465A1

  公开（公告）日：2019-01-03

  Provided herein are compositions and methods for adoptive cell therapy comprising engineered immune cells that express a tumor antigen-targeted chimeric antigen receptor and a prodrug converting enzyme.

  本文提供了一种包括表达肿瘤抗原靶向嵌合抗原受体和一种前药转化酶的工程免疫细胞的细胞治疗组合物和方法。
• Mild preparation of cephalosporin allyl and p-methoxybenzyl esters using diazoalkanes
  作者：Sherman T. Waddell、Gina M. Santorelli

  DOI：10.1016/0040-4039(96)00183-9

  日期：1996.3

  Vinyl or p-methoxyphenyldiazomethane reacts rapidly with cephalosporins in ether/methylene chloride cosolvent to give the C-9 allyl and p-methoxybenzyl esters, respectively, in good yields, with no isomerization of the double bond to Δ-2.

  乙烯基或对甲氧基苯基重氮甲烷与头孢菌素在乙醚/二氯甲烷助溶剂中快速反应，分别以高收率分别得到C-9烯丙基酯和对甲氧基苄基酯，而双键没有异构化为Δ-2。
• Synthesis of acylhydrazido-substituted cephems. Design of cephalosporin-vinca alkaloid prodrugs: substrates for an antibody targeted enzyme
  作者：Louis N. Jungheim、Timothy A. Shepherd、Damon L. Meyer

  DOI：10.1021/jo00034a027

  日期：1992.4

  Cephalosporin 20 substituted at the C-3' position with the potent oncolytic agent desacetylvinblastine hydrazide (3) was synthesized as a potential prodrug for the treatment of solid tumors. The design of this novel prodrug was based on the knowledge that hydrolysis of a cephalosporin's beta-lactam bond can result in the expulsion of the C-3' substituent. Proper selection of the linkage used to join the cephem to the vinca, e.g., 8 vs 20, provided a releasable form of the drug as well as a chemically stable prodrug. We envisioned the conversion of prodrug to free vinca to be mediated by an immunoconjugate, consisting of a beta-lactamase enzyme covalently attached to a monoclonal antibody, which has been prelocalized at the tumor. Treatment of candidate prodrugs with the P99 beta-lactamase enzyme isolated from Enterobacter cloacae 265A efficiently catalyzed their conversion to the free drug form. A study of model compounds 11 and 18 indicated that cephem 1-beta-sulfoxide 18 was a better substrate for the enzyme than its sulfide counterpart 11. This finding prompted the synthesis of cephem sulfoxide 20 which was efficiently accomplished via condensation of desacetylvinblastine hydrazide with the cephalothin derived cephem 3'-p-nitrophenyl carbonate 15.
• Preparation of ceph-3-em esters unaccompanied by .DELTA.3 .fwdarw. .DELTA.2 isomerization of the cephalosporin
  作者：Shahriar Mobashery、Michael Johnston

  DOI：10.1021/jo00374a045

  日期：1986.11