3'-azido-2',3'-dideoxy-5-(trifluoromethyl)uridine | 87190-84-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 3'-azido-2',3'-dideoxy-5-(trifluoromethyl)uridine
• 英文别名: 3'-Azido-2',3'-dideoxy-5-trifluoromethyluridine；1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-(trifluoromethyl)pyrimidine-2,4-dione
• CAS: 87190-84-9
• 化学式: C₁₀H₁₀F₃N₅O₄
• 分子量: 321.216
• InChiKey: LYWDBOUHROZMIU-RRKCRQDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  93.2
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3'-azido-2',3'-dideoxy-5-(trifluoromethyl)uridine 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以72%的产率得到3'-amino-2',3'-dideoxy-5-(trifluoromethyl)uridine
  参考文献：
  名称：

  Synthesis and biological activity of various 3'-azido and 3'-amino analogs of 5-substituted pyrimidine deoxyribonucleosides

  摘要：

  Various new 5-substituted 3'-azido- and 3'-amino derivatives of 2'-deoxyuridine and 2'-deoxycytidine have been synthesized and biologically evaluated. Among these compounds, 3'-amino-2',3'-dideoxy-5-fluorouridine (3), 3'-amino-2',3'-dideoxycytidine (7a), and 3'-amino-2',3'-dideoxy-5-fluorocytidine (7c) were found to be the most active against murine L1210 and sarcoma 180 neoplastic cells in vitro, with an ED50 of 15 and 1 microM, 0.7 and 4 microM, and 10 and 1 microM, respectively. The 3'-azido derivatives, 2 and 6c, were less active in comparison with their 3'-amino counterparts. In addition, the 5-fluoro-3'-amino nucleosides, 3 and 7c, were tested against L1210 leukemia bearing CDF1 mice. Our preliminary findings indicate that compound 7c (6 X 200 mg/kg) was as active as the positive control, 5-fluorouracil (6 X 20 mg/kg), yielding a T/C X 100 of 146 and 129, respectively. However, 3 was found to be inactive in this experiment.

  DOI：

  10.1021/jm00366a006
• 作为产物：
  描述：

  三氟胸苷 在 吡啶 、 叠氮化锂 、 四乙基氟化铵水合物 、 甲基磺酰氯 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 反应 17.0h， 生成 3'-azido-2',3'-dideoxy-5-(trifluoromethyl)uridine
  参考文献：
  名称：

  Joshi, Bhalchandra V.; Rao, T. Sudhakar; Reese, Colin B., Journal of the Chemical Society. Perkin transactions I, 1992, # 19, p. 2537 - 2544

  摘要：

  DOI：

文献信息

• [EN] NEW ANTI-MYCOBACTERIAL DRUGS AGAINST TUBERCULOSIS<br/>[FR] NOUVEAUX MÉDICAMENTS ANTI-MYCOBACTÉRIENS CONTRE LA TUBERCULOSE
  申请人：UNIV GEORGIA

  公开号：WO2013148174A1

  公开（公告）日：2013-10-03

  The present invention relates to the field of anti-mycobacterial therapeutics, in particular the treatment of tuberculosis, especially including pulmonary multidrug-resistant tuberculosis (MDR-TB), with applications in extensively drug-resistant tuberculosis (XDR-TB) and extremely drug-resistant tuberculosis (XXDR-TB), preferably in combination therapy.

  本发明涉及抗结核治疗领域，特别是肺部多药耐药结核病（MDR-TB）的治疗，包括广泛耐药结核病（XDR-TB）和极度耐药结核病（XXDR-TB），优选采用联合治疗。
• Pyridinone Diketo Acids: Inhibitors of HIV Replication in Combination Therapy
  申请人：Nair Vasu

  公开号：US20100092427A1

  公开（公告）日：2010-04-15

  A new class of diketo acids constructed on pyridinone scaffolds, designed as inhibitors of HTV replication through inhibition of HIV integrase, is described. These compounds are useful in the prevention or treatment of infection by HIV and in the treatment of AIDS and ARC, either as the compounds, or as pharmaceutically acceptable salts, with pharmaceutically acceptable carriers, used alone or in combination with antivirals, immunomodulators, antibiotics, vaccines, and other therapeutic agents, especially other anti-HIV compounds (including other anti-HIV integrase agents), which can be used to create combination anti-HIV cocktails. Methods of treating AIDS and ARC and methods of treating or preventing infection by HIV are also described. Compounds of the present application include those of formula I and include tautomers, regioisomers, geometric isomers, and pharmaceutically acceptable salts thereof, wherein the pyridinone scaffold and R groups are as otherwise defined in the specification. These are combined, with any number of typical other anti-HIV agents (including other integrase-based anti-HIV agents) and other combination therapeutic agents described herein, to provide an effective treatment modality for HIV infections, including AIDS and ARC.

  本文描述了一类新型的二酮酸，构建在吡啶酮支架上，设计用于通过抑制HIV整合酶来抑制HIV复制。这些化合物可用于预防或治疗HIV感染以及治疗AIDS和ARC，可以作为化合物本身或与药物载体结合使用，或与其他抗病毒药物、免疫调节剂、抗生素、疫苗和其他治疗剂联合使用，尤其是其他抗HIV化合物（包括其他抗HIV整合酶剂），以形成联合抗HIV药物组合。本申请的化合物包括公式I中的化合物和其中的互变异构体、区域异构体、几何异构体和其药学上可接受的盐，其中吡啶酮支架和R基在规范中另有定义。这些化合物与任意数量的典型其他抗HIV药物（包括其他基于整合酶的抗HIV药物）和其他联合治疗剂联合使用，提供了一种有效的治疗HIV感染的治疗模式，包括AIDS和ARC的治疗方法。
• PYRIDINONE HYDROXYCYCLOPENTYL CARBOXAMIDES: HIV INTEGRASE INHIBITORS WITH THERAPEUTIC APPLICATIONS
  申请人：Nair Vasu

  公开号：US20120282218A1

  公开（公告）日：2012-11-08

  New chiral and achiral oxy-substituted cyclopentyl pyridinone diketocarboxamides and their derivatives and methods for their preparations are disclosed. The compounds include tautomers, regioisomers and geometric isomers. These complex carboxamides are designed as inhibitors of HIV replication through inhibition of HIV integrase. The compounds are useful in the prevention or treatment of infection by HIV and in the treatment of AIDS and ARC, either as the compounds, or as pharmaceutically acceptable salts, with pharmaceutically acceptable carriers, used alone or in combination with antivirals, immunomodulators, antibiotics, vaccines, and other therapeutic agents, especially other anti-HIV compounds (including other anti-HIV integrase agents), which can be used to create combination anti-HIV cocktails. Methods of treating AIDS and ARC and methods of treating or preventing infection by HIV are also described.

  本发明公开了新的手性和非手性氧取代的环戊基吡啶酮二酮羧酰胺及其衍生物的制备方法。这些化合物包括互变异构体、区域异构体和几何异构体。这些复杂的羧酰胺被设计为通过抑制HIV整合酶来抑制HIV复制的抑制剂。这些化合物可用于预防或治疗HIV感染以及治疗艾滋病和ARC，可以作为化合物或药学上可接受的盐，与药学上可接受的载体一起使用，单独使用或与抗病毒药物、免疫调节剂、抗生素、疫苗和其他治疗剂（尤其是其他抗HIV化合物，包括其他抗HIV整合酶剂）组合使用，以创建组合抗HIV鸡尾酒。还描述了治疗艾滋病和ARC以及治疗或预防HIV感染的方法。
• NEW ANTI-MYCOBACTERIAL DRUGS AGAINST TUBERCULOSIS
  申请人：UNIVERSITY OF GEORGIA RESEARCH FOUNDATION, INC.

  公开号：US20150050237A1

  公开（公告）日：2015-02-19

  The present invention relates to the field of anti-mycobacterial therapeutics, in particular the treatment of tuberculosis, especially including pulmonary multidrug-resistant tuberculosis (MDR-TB), with applications in extensively drug-resistant tuberculosis (XDR-TB) and extremely drug-resistant tuberculosis (XXDR-TB), preferably in combination therapy.

  本发明涉及抗结核菌治疗领域，特别是肺部多药耐药结核病（MDR-TB）的治疗，包括广泛耐药结核病（XDR-TB）和极度耐药结核病（XXDR-TB），优选采用联合治疗方法。
• Therapeutic nucleosides
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0217580A2

  公开（公告）日：1987-04-08

  The present invention relates to certain novel 3'- azidonucleosides and pharmaceutically acceptable derivatives thereof; the use of certain 3'-azidonucleosides, their pharmaceutically acceptable derivatives and therapeutic combinations containing them, in therapy, particularly in the treatment and prophylaxis of gram negative bacterial infections and retroviral infections, especially AIDS; to processes for the preparation of 3'-azidonucleosides; and to formulations containing them.

  本发明涉及某些新型 3'-叠氮核苷及其药学上可接受的衍生物；某些 3'-叠氮核苷、其药学上可接受的衍生物和含有它们的治疗组合物在治疗中的用途，特别是在革兰氏阴性细菌感染和逆转录病毒感染（尤其是艾滋病）的治疗和预防中的用途；3'-叠氮核苷的制备工艺；以及含有它们的制剂。