7-cyanonaphthalen-2-yl trifluoromethanesulfonate | 188616-78-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 7-cyanonaphthalen-2-yl trifluoromethanesulfonate
• 英文别名: 7-cyano-2-naphthyl trifluoromethanesulfonate；(7-cyanonaphthalen-2-yl) trifluoromethanesulfonate
• CAS: 188616-78-6
• 化学式: C₁₂H₆F₃NO₃S
• 分子量: 301.246
• InChiKey: RBTTUQHWNJRRRT-UHFFFAOYSA-N

物化性质

• 熔点：
  75.1 °C(Solv: dichloromethane (75-09-2); heptane (142-82-5))
• 沸点：
  415.4±45.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  75.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  7-cyanonaphthalen-2-yl trifluoromethanesulfonate 在 bis-triphenylphosphine-palladium(II) chloride 、 N-溴代丁二酰亚胺(NBS) 、 十二/十四烷基二甲基氧化胺 、 三乙酰氧基硼氢化钠 、 溶剂黄146 、 lithium chloride 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 生成 7-({4-[(1-tert-butoxycarbonyl-4-piperidyl)oxy]anilino}methyl)naphthalene-2-carbonitrile
  参考文献：
  名称：

  Design, synthesis and structure–Activity relationships of benzoxazinone-Based factor Xa inhibitors

  摘要：

  A series of benzoxazinone derivatives was designed and synthesized as factor Xa inhibitors. We demonstrated that the naphthyl moiety in the aniline-based compounds I and 2 can be replaced with benzene-fused heterobicycles and biaryls to give factor Xa inhibitors with improved trypsin selectivity. The P4 modifications lead to monoamidines which are moderately active. The benzoxazinones 41-45 are potent against factor Xa, retain the improved trypsin selectivity of the corresponding aniline-based compounds, and show strong antithrombotic effect dose responsively. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(02)00927-7
• 作为产物：
  描述：

  7-羟基-2-萘甲腈 生成 7-cyanonaphthalen-2-yl trifluoromethanesulfonate
  参考文献：
  名称：

  Pharmaceutical compounds

  摘要：

  这项发明涉及到式(I)的化合物，其中R1至R12，—W—V—，—X—Y—，m和n的值如权利要求1中定义的，它们的制备和用作药物。

  公开号：

  US20040122001A1

文献信息

• A Short Synthesis of the Factor-Xa Inhibitor DX-9065a using palladium-catalyzed key steps
  作者：Christiane Kehr、Richard Neidlein、Richard A. Engh、Hans Brandsretter、Ralf Kucznierz、Herbert Leinert、Klaus Marzenell、Klaus Strein、Wolfgang Von Der Saal

  DOI：10.1002/hlca.19970800322

  日期：1997.5.12

  We describe a new, efficient synthesis of DX-9065a (4), a potent inhibitor of the blood coagulation enzyme factor Xa (fXa) which has previously been prepared in more than 20 steps. We saved approximately 10 steps starting with a Pd-catalyzed cyanation of the triflate 10 of 7-methoxynaphthalen-2-ol (9). After cleavage of the MeO group with boron tribromide, the triflate 6 was coupled to acrylate 5 in

  我们描述了一种新的，高效的DX-9065a（4）合成方法，DX-9065a是一种有效的凝血酶因子Xa（fXa）抑制剂，以前已在20多个步骤中进行了制备。我们从7-甲氧基萘-2-醇（9）的三氟甲磺酸酯10的钯催化氰化反应开始，节省了大约10个步骤。在用三溴化硼裂解MeO基团之后，三氟甲磺酸酯6在Heck反应（3）中与丙烯酸酯5偶联。随后的转换导致了DX-9065a。
• Dicationic DNA-targeted antiprotozoal agents: Naphthalene replacement of benzimidazole
  作者：Sarah Chackal-Catoen、Yi Miao、W. David Wilson、Tanja Wenzler、Reto Brun、David W. Boykin

  DOI：10.1016/j.bmc.2006.07.024

  日期：2006.11

  A series of naphthalene analogues of highly active benzimidazole diamidines were synthesized using sequential Stille and Suzuki coupling reactions for preparation of the bis-nitrile intermediates. All of the diamidines showed strong DNA affinities as judged by high Delta T-m values with poly(dA-dT). The dicationic compounds were quite active in vitro versus Trypanosoma brucei rhodesiense (T. b. r.) exhibiting IC50 values ranging from 4 to 98 nM. These compounds were also active versus Plasmodium falciparum (P. f) giving IC50 values ranging from 4 to 33 nM. Two of the compounds showed good activity in vivo in the STIB900 model for acute African trypanosomiasis; one gave 3/4 cures and the other gave 4/4 cures on ip dosage of 20 mg/kg for 4 days. The amidoxime prodrugs of the naphthalene analogues were essentially ineffective. (c) 2006 Elsevier Ltd. All rights reserved.
• PHARMACEUTICAL COMPOUNDS
  申请人：ELI LILLY AND COMPANY

  公开号：EP1345930A2

  公开（公告）日：2003-09-24
• [EN] PHARMACEUTICAL COMPOUNDS<br/>[FR] COMPOSES PHARMACEUTIQUES
  申请人：LILLY CO ELI

  公开号：WO2002050067A2

  公开（公告）日：2002-06-27

  This invention relates to compounds of formula (I) where R?1 to R12¿, -W-V-, -X-Y-, m and n have the values defined in claim 1, their preparation and use as pharmaceuticals.