(6R,7R)-3-{4-[4-(3,4-Dimethoxy-phenyl)-2,3-dimethyl-butyl]-2-methoxy-phenoxymethyl}-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid | 500904-35-8

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (6R,7R)-3-{4-[4-(3,4-Dimethoxy-phenyl)-2,3-dimethyl-butyl]-2-methoxy-phenoxymethyl}-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS: 500904-35-8
• 化学式: C₃₇H₄₂N₂O₁₀S
• 分子量: 706.814
• InChiKey: LVVCKLDIOQDLPD-UMKPNEIDSA-N

反应信息

• 作为反应物：
  描述：

  (6R,7R)-3-{4-[4-(3,4-Dimethoxy-phenyl)-2,3-dimethyl-butyl]-2-methoxy-phenoxymethyl}-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 在 β-lactamase 作用下， 以 二甲基亚砜 为溶剂， 生成 (±)-1-(4-hydroxy-3-methoxyphenyl)-(2R,3S)-dimethyl-4-(3,4-dimethoxyphenyl)butane
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of a cephalosporin–monohydroguaiaretic acid prodrug activated by a monoclonal antibody–β-lactamase conjugate

  摘要：

  A novel cephalosporin derivative of monohydroguaiaretic acid (cephem-M3N, 7) was synthesized and found to possess anticancer activity against human leukemia (K562), breast carcinoma (MCF7), human lung cancer (A549), human colon cancer (Colo205) and pancreatic cancer cells (Capan2 and MiaPaCa2). A tumor targeting fusion protein (dsFv3-beta-lactamase) was also used in conjunction with cephem-based M3N 7 and its potency toward K562, MCF7, A549, Colo205, Capan2. and MiaPaCa2 was found to approach that of the free M3N (4). In the presence of dsFv3-beta-lactamase. tumor cells were found to be much more susceptible to conjugate 7 than normal human embryonic lung (HEL) cells and normal fibroblasts (Hef522). These notions provide a new approach to the use of nordihydroguaiaretic acid (NDGA) and its derivatives for antitumor therapy. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00140-2
• 作为产物：
  描述：

  (6R,7R)-3-{4-[4-(3,4-Dimethoxy-phenyl)-2,3-dimethyl-butyl]-2-methoxy-phenoxymethyl}-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester 在 苯甲醚 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以74%的产率得到(6R,7R)-3-{4-[4-(3,4-Dimethoxy-phenyl)-2,3-dimethyl-butyl]-2-methoxy-phenoxymethyl}-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of a cephalosporin–monohydroguaiaretic acid prodrug activated by a monoclonal antibody–β-lactamase conjugate

  摘要：

  A novel cephalosporin derivative of monohydroguaiaretic acid (cephem-M3N, 7) was synthesized and found to possess anticancer activity against human leukemia (K562), breast carcinoma (MCF7), human lung cancer (A549), human colon cancer (Colo205) and pancreatic cancer cells (Capan2 and MiaPaCa2). A tumor targeting fusion protein (dsFv3-beta-lactamase) was also used in conjunction with cephem-based M3N 7 and its potency toward K562, MCF7, A549, Colo205, Capan2. and MiaPaCa2 was found to approach that of the free M3N (4). In the presence of dsFv3-beta-lactamase. tumor cells were found to be much more susceptible to conjugate 7 than normal human embryonic lung (HEL) cells and normal fibroblasts (Hef522). These notions provide a new approach to the use of nordihydroguaiaretic acid (NDGA) and its derivatives for antitumor therapy. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00140-2