8-Oxo-7-phenylacetylamino-3-vinyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• 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: 8-Oxo-7-phenylacetylamino-3-vinyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• 英文别名: 3-Ethenyl-8-oxo-7-[(phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid；3-ethenyl-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• 化学式: C₁₇H₁₆N₂O₄S
• 分子量: 344.391
• InChiKey: AGAOMWQWVIJILM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,N'-diisopropyl-O-benzhydrylisourea 、 8-Oxo-7-phenylacetylamino-3-vinyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 以 四氢呋喃 为溶剂， 反应 17.0h， 以79%的产率得到8-Oxo-7-phenylacetylamino-3-vinyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
  参考文献：
  名称：

  N,N'-Diisopropyl-O-Diphenylmethyl Isourea: A Mild and Convenient Alkylating Agent for the Formation of Cephalosporin Derivatives

  摘要：

  N,N'-Diisopropyl-O-diphenylmethyl isourea reacts with cephalosporin-4-carboxylic acid in tetrahydrofuran at room temperature to give the diphenylmethyl (DPM) ester in good yields without isomerization of the double bond from C-3 to C-2.

  DOI：

  10.1080/00397919808007035
• 作为产物：
  描述：

  4-methoxybenzyl 7-phenylacetamido-3-vinyl-3-cephem-4-carboxylate 在 iodotrimethylsilane*triphenylphosphine 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以86%的产率得到8-Oxo-7-phenylacetylamino-3-vinyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  用碘三甲基-硅烷-三苯基膦轻松去除对甲氧基苄基和二苯甲酯

  摘要：

  摘要 使用碘三甲基硅烷 (TMSI)-三苯基膦 (TPP) 在二氯甲烷中在室温下将头孢菌素衍生物的二苯甲基 (DPM) 和对甲氧基苄基 (PMB) 酯转化为相应的羧酸。

  DOI：

  10.1080/00397919908085986

文献信息

• New derivatives of cephalosporin for treating cancer
  申请人：Institut Curie

  公开号：EP2926815A1

  公开（公告）日：2015-10-07

  The present invention relates to a new class of cephalosporin derivatives of formula (I), notably having CXCR4 receptor antagonist effect, useful as a therapeutic agent for treating cancer, in particular for treating breast cancer, lung cancer and uveal melanoma. The invention further relates to a pharmaceutical composition comprising a compound of formula (I) and an additional antitumor drug for treating cancer.

  本发明涉及一类新的式(I)头孢菌素衍生物，特别是具有 CXCR4 受体拮抗剂作用的衍生物，可作为治疗癌症，特别是治疗乳腺癌、肺癌和葡萄膜黑色素瘤的治疗剂。本发明还涉及一种药物组合物，该药物组合物包含式（I）化合物和另一种治疗癌症的抗肿瘤药物。
• Derivatives of cephalosporin for treating cancer
  申请人：INSTITUT CURIE

  公开号：US10821114B2

  公开（公告）日：2020-11-03

  The present invention relates to a new class of cephalosporin derivatives of formula (I), notably having CXCR4 receptor antagonist effect, useful as a therapeutic agent for treating cancer, in particular for treating breast cancer, lung cancer and uveal melanoma. The invention further relates to a pharmaceutical composition comprising a compound of formula (I) and an additional antitumor drug for treating cancer.

  本发明涉及一类新的式(I)头孢菌素衍生物，特别是具有 CXCR4 受体拮抗剂作用的衍生物，可作为治疗癌症，特别是治疗乳腺癌、肺癌和葡萄膜黑色素瘤的治疗剂。本发明还涉及一种药物组合物，该药物组合物包含式（I）化合物和另一种治疗癌症的抗肿瘤药物。
• NEW DERIVATIVES OF CEPHALOSPORIN FOR TREATING CANCER
  申请人：Institut Curie

  公开号：EP3125901A1

  公开（公告）日：2017-02-08
• DERIVATIVES OF CEPHALOSPORIN FOR TREATING CANCER
  申请人：Institut Curie

  公开号：EP3125901B1

  公开（公告）日：2018-06-06
• [EN] NEW DERIVATIVES OF CEPHALOSPORIN FOR TREATING CANCER<br/>[FR] NOUVEAUX DÉRIVÉS DE CÉPHALOSPORINE POUR LE TRAITEMENT DU CANCER
  申请人：INST CURIE

  公开号：WO2015150516A1

  公开（公告）日：2015-10-08

  The present invention relates to a new class of cephalosporin derivatives of formula (I), notably having CXCR4 receptor antagonist effect, useful as a therapeutic agent for treating cancer, in particular for treating breast cancer, lung cancer and uveal melanoma. The invention further relates to a pharmaceutical composition comprising a compound of formula (I) and an additional antitumor drug for treating cancer.