(1R,3S,4S,11S)-8-(benzyloxy)-11-[(tert-butyldimethylsilyl)oxy]-4-(dimethylamino)-19-fluoro-12-hydroxy-10,14-dioxo-6-oxa-7-azapentacyclo[11.8.0.0.(3,11)0.(5,9)0(15,20)]henicosa-5-(9),7,12,15(20),16,18-hexaen-16-yl tert-butyl carbonate | 1207283-57-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (1R,3S,4S,11S)-8-(benzyloxy)-11-[(tert-butyldimethylsilyl)oxy]-4-(dimethylamino)-19-fluoro-12-hydroxy-10,14-dioxo-6-oxa-7-azapentacyclo[11.8.0.0.(3,11)0.(5,9)0(15,20)]henicosa-5-(9),7,12,15(20),16,18-hexaen-16-yl tert-butyl carbonate
• CAS: 1207283-57-5
• 化学式: C₃₉H₄₇FN₂O₉Si
• 分子量: 734.894
• InChiKey: GMVVJZKBZFVBNA-JHKYAHIZSA-N

物化性质

• 沸点：
  788.9±60.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.15
• 重原子数：
  52.0
• 可旋转键数：
  7.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  137.63
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (1R,3S,4S,11S)-8-(benzyloxy)-11-[(tert-butyldimethylsilyl)oxy]-4-(dimethylamino)-19-fluoro-12-hydroxy-10,14-dioxo-6-oxa-7-azapentacyclo[11.8.0.0.(3,11)0.(5,9)0(15,20)]henicosa-5-(9),7,12,15(20),16,18-hexaen-16-yl tert-butyl carbonate 在 硫酸 、 palladium 10% on activated carbon 、 氢氟酸 、 氢气 、 硝酸 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 乙腈 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 19.5h， 生成 (4S,4aS,5aR,12aS)-4-(dimethylamino)-7-fluoro-3,10,12,12a-tetrahydroxy-9-nitro-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
  参考文献：
  名称：

  Fluorocyclines. 1. 7-Fluoro-9-pyrrolidinoacetamido-6-demethyl-6-deoxytetracycline: A Potent, Broad Spectrum Antibacterial Agent

  摘要：

  This and the accompanying report (DOI: 10.1021/jm201467r) describe the design, synthesis, and evaluation of a new generation of tetracycline antibacterial agents, 7-fluoro-9-substituted-6-demethyl-6-deoxytetracyclines ("fluorocyclines"), accessible through a recently developed total synthesis approach. These fluorocyclines possess potent antibacterial activities against multidrug resistant (MDR) Gram-positive and Gram-negative pathogens. One of the fluorocyclines, 7-fluoro-9-pyrrolidinoacetamido-6-demethyl-6-deoxytetracycline (17j, also known as TP-434, 50th Interscience Conference on Antimicrobial Agents and Chemotherapy Conference, Boston, MA, September 12-15, 2010, poster F1-2157), is currently undergoing phase 2 clinical trials in patients with complicated intra-abdominal infections (cIAI).

  DOI：

  10.1021/jm201465w
• 作为产物：
  描述：

  phenyl 3-fluoro-6-methoxy-2-methylbenzoate 在 4-二甲氨基吡啶 、 四甲基乙二胺 、 三溴化硼 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 4.08h， 生成 (1R,3S,4S,11S)-8-(benzyloxy)-11-[(tert-butyldimethylsilyl)oxy]-4-(dimethylamino)-19-fluoro-12-hydroxy-10,14-dioxo-6-oxa-7-azapentacyclo[11.8.0.0.(3,11)0.(5,9)0(15,20)]henicosa-5-(9),7,12,15(20),16,18-hexaen-16-yl tert-butyl carbonate
  参考文献：
  名称：

  Fluorocyclines. 1. 7-Fluoro-9-pyrrolidinoacetamido-6-demethyl-6-deoxytetracycline: A Potent, Broad Spectrum Antibacterial Agent

  摘要：

  This and the accompanying report (DOI: 10.1021/jm201467r) describe the design, synthesis, and evaluation of a new generation of tetracycline antibacterial agents, 7-fluoro-9-substituted-6-demethyl-6-deoxytetracyclines ("fluorocyclines"), accessible through a recently developed total synthesis approach. These fluorocyclines possess potent antibacterial activities against multidrug resistant (MDR) Gram-positive and Gram-negative pathogens. One of the fluorocyclines, 7-fluoro-9-pyrrolidinoacetamido-6-demethyl-6-deoxytetracycline (17j, also known as TP-434, 50th Interscience Conference on Antimicrobial Agents and Chemotherapy Conference, Boston, MA, September 12-15, 2010, poster F1-2157), is currently undergoing phase 2 clinical trials in patients with complicated intra-abdominal infections (cIAI).

  DOI：

  10.1021/jm201465w

文献信息

• [EN] C7-FLUORO SUBSTITUTED TETRACYCLINE COMPOUNDS<br/>[FR] COMPOSÉS DE TÉTRACYCLINE C7-FLUOROSUBSTITUÉE
  申请人：TETRAPHASE PHARMACEUTICALS INC

  公开号：WO2010017470A1

  公开（公告）日：2010-02-11

  The present invention is directed to a compound represented by Structural Formula (A): or a pharmaceutically acceptable salt thereof. The variables for Structural Formula (A) are defined herein. Also described is a pharmaceutical composition comprising the compound of Structural Formula (A) and its therapeutic use.

  本发明涉及一种由结构式（A）表示的化合物，或其药学上可接受的盐。结构式（A）的变量在此处定义。还描述了包括结构式（A）化合物的药物组合物及其治疗用途。
• J. Med. Chem. 2012, 55, 597-605
  作者：

  DOI：——

  日期：——