N-(cyclohexyl)-5-nitrofuran-2-carboxamide | 15182-30-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: N-(cyclohexyl)-5-nitrofuran-2-carboxamide
• 英文别名: 5-nitro-furan-2-carboxylic acid cyclohexylamide；SKI-71763；N-Cyclohexyl-5-nitro-2-furamide；2-Furancarboxamide, N-cyclohexyl-5-nitro-；N-cyclohexyl-5-nitrofuran-2-carboxamide
• CAS: 15182-30-6
• 化学式: C₁₁H₁₄N₂O₄
• mdl: MFCD00451494
• 分子量: 238.243
• InChiKey: HDJQCPXCTJSUPW-UHFFFAOYSA-N

物化性质

• 沸点：
  414.2±30.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  88.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(cyclohexyl)-5-nitrofuran-2-carboxamide 在 盐酸 、 5%-palladium/activated carbon 、 氢气 、 碳酸氢钠 、 sodium carbonate 、 sodium hydroxide 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 生成 N-(cyclohexyl)-5-((2-methyl-4-neopentylphenyl)diazenyl)furan-2-carboxamide
  参考文献：
  名称：

  一种Raf 激酶抑制剂及其在癌症治疗中的应用

  摘要：

  本发明公开了一种Raf激酶抑制剂式Ⅰ及其在癌症治疗中的应用，其中：R1、R2、R3、R4各自独立的选自H、Br或CH3。体外药理实验证实本发明化合物式Ⅰ具有Raf‑1激酶的抑制活性，可以抑制A498、HT‑29、COLO‑205活性。与Raf激酶抑制剂有关的癌症可以是黑色素瘤、肝癌、肾癌、急性白血病、非小细胞肺癌、前列腺癌、甲状腺癌、皮肤癌、结肠直肠癌、胰腺癌、卵巢癌、乳腺癌、骨髓增生异常综合症、食管癌、胃癌或间皮瘤等。

  公开号：

  CN108456186A
• 作为产物：
  描述：

  5-硝基-2-糠酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 N-(cyclohexyl)-5-nitrofuran-2-carboxamide
  参考文献：
  名称：

  A Class of 5-Nitro-2-furancarboxylamides with Potent Trypanocidal Activity against Trypanosoma brucei in Vitro

  摘要：

  Recently, the World Health Organization approved the nifurtimox-eflornithine combination therapy for the treatment of human African trypanosomiasis, renewing interest in nitroheterocycle therapies for this and associated diseases. In this study, we have synthesized a series of novel 5-nitro-2-furancarboxylamides that show potent trypanocidal activity, similar to 1000-fold more potent than nifurtimox against in vitro Trypanosoma brucei with very low cytotoxicity against human He La cells. More importantly, the most potent analogue showed very limited cross-resistance to nifurtimox-resistant cells and vice versa. This implies that our novel, relatively easy to synthesize and therefore cheap, 5-nitro-2-furancarboxylamides are targeting a different, but still essential, biochemical process to those targeted by nifurtimox or its metabolites in the parasites. The significant increase in potency (smaller dose probably required) has the potential for greatly reducing unwanted side effects and also reducing the likelihood of drug resistance. Collectively, these findings have important implications for the future therapeutic treatment of African sleeping sickness.

  DOI：

  10.1021/jm301215e

文献信息

• Heterocyclic amides with anti-tuberculosis activity
  申请人：Lee E. Richard

  公开号：US20050222408A1

  公开（公告）日：2005-10-06

  Compounds having the general structure: wherein A is selected from the group consisting of oxygen, sulfur, and NR 15 , and R 15 is selected from the group consisting of H, alkyl, aryl, substituted alkyl, and substituted aryl; B,D, and E are each independently selected from the group consisting of CH, nitrogen, sulfur and oxygen; R 1 is selected from the group consisting of nitro, halo, alkyl ester, arylsulfanyl, arylsulfinyl, arylsulfonyl and sulfonic acid; t is an integer from 1 to 3; and X is a substituted amide, and methods of using the novel compounds for treating infections caused by microorganisms, including Mycobacterium tuberculosis.

  具有一般结构的化合物：其中A从氧、硫和NR15组成的群体中选择，R15从H、烷基、芳基、取代烷基和取代芳基组成的群体中选择；B、D和E分别独立地从CH、氮、硫和氧组成的群体中选择；R1从硝基、卤素、烷基酯、芳基硫醚、芳基亚砜、芳基砜基和磺酸中选择；t为1到3的整数；X为取代酰胺，并且使用这些新化合物治疗由微生物引起的感染的方法，包括结核分枝杆菌。
• PYRIDAZINONES AND FURAN-CONTAINING COMPOUNDS
  申请人：Djaballah Hakim

  公开号：US20100210649A1

  公开（公告）日：2010-08-19

  The present invention is directed to pyridazinone compounds of formula (I) and furan compounds of formula (II), pharmaceutical compositions of compounds of formula (I) and (II), kits containing these compounds, methods of syntheses, and a method of treatment of a proliferative disease in a subject by administration of a therapeutically effective amount of a compound of formulae (I) or (II). Both classes of compounds were identified through screening of a collection of small molecule libraries.

  本发明涉及式(I)的吡啶二酮化合物和式(II)的呋喃化合物，以及式(I)和(II)化合物的制药组合物、包含这些化合物的试剂盒、合成方法，以及通过给予式(I)或(II)化合物的治疗有效量来治疗受体内增生性疾病的方法。这两类化合物是通过筛选小分子库的集合而确定的。
• [EN] HETEROCYCLIC AMIDES WITH ANTI-TUBERCULOSIS ACTIVITY<br/>[FR] AMIDES HETEROCYCLIQUES A ACTIVITE ANTI-TUBERCULINIQUE
  申请人：UNIV TENNESSEE RES FOUNDATION

  公开号：WO2005007625A3

  公开（公告）日：2005-12-29
• Synthesis and Evaluation of Nitrofuranylamides as Novel Antituberculosis Agents
  作者：Rajendra P. Tangallapally、Raghunandan Yendapally、Robin E. Lee、Kirk Hevener、Victoria C. Jones、Anne J. M. Lenaerts、Michael R. McNeil、Yuehong Wang、Scott Franzblau、Richard E. Lee

  DOI：10.1021/jm049972y

  日期：2004.10.1

  In an effort to develop new and more potent therapies to treat tuberculosis, a library of compounds was screened for M. tuberculosis UDP-Gal mutase inhibition. Nitrofuranylamide 1 was identified as a hit in this screen, possessing good antituberculosis activity. This paper describes the synthesis and evaluation of an expanded set of nitrofaranylamides. We have discovered a number of nitrofaranylamides with submicromolar M. tuberculosis MIC values and acceptable therapeutic indexes. The MIC activity did not correlate with UDP-Gal mutase inhibition, suggesting an alternative primary cellular target was responsible for the antituberculosis activity. The compounds were only active against mycobacteria of the tuberculosis complex. On the basis of these results, four compounds were selected for in vivo testing in a mouse model of tuberculosis infection, and of these compounds one showed significant antituberculosis activity.
• Nitrofuryl Heterocycles. VI.¹ l-Alkyl-and l-Aryl-5-(5-nitro-2-furyl)tetrazoles
  作者：Harry R. Snyder

  DOI：10.1021/jm00316a052

  日期：1967.7