N-(3-chloro-1,4-dioxo-1,4-dihydro-[2]naphthyl)-butyramide | 95612-66-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(3-chloro-1,4-dioxo-1,4-dihydro-[2]naphthyl)-butyramide
• 英文别名: 2-Butyrylamino-3-chlor-[1,4]naphthochinon；N-(3-Chlor-1,4-dioxo-1,4-dihydro-[2]naphthyl)-butyramid；N-(3-chloro-1,4-dioxonaphthalen-2-yl)butanamide
• CAS: 95612-66-1
• 化学式: C₁₄H₁₂ClNO₃
• 分子量: 277.707
• InChiKey: QRIWUMQXJVSZPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  63.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3-chloro-1,4-dioxo-1,4-dihydro-[2]naphthyl)-butyramide 在 sodium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 7.0h， 生成 2-propyl-3-(2,2,6,6-tetramethyl-4-piperidyl)naphtho<1,2-d>imidazole-6,11-dione
  参考文献：
  名称：

  Litvin, B. L.; Kolesnikov, V. T., Journal of Organic Chemistry USSR (English Translation), 1986, p. 1560 - 1566

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-二氯-1,4-萘醌 在 盐酸 、 ammonium hydroxide 、 乙醇 作用下， 生成 N-(3-chloro-1,4-dioxo-1,4-dihydro-[2]naphthyl)-butyramide
  参考文献：
  名称：

  Preparation of Some Imidazole Derivatives of 1,4-Naphthoquinone

  摘要：

  DOI：

  10.1021/ja01645a028

文献信息

• Synthesis and Cytotoxicity of 1,2-Disubstituted Naphth[2,3-<i>d</i>]imidazole-4,9-diones and Related Compounds
  作者：Sheng-Chu Kuo、Toshiro Ibuka、Li-Jiau Huang、Jin-Cherng Lien、Shyue-Ren Yean、Shung-Chieh Huang、Daniel Lednicer、Susan Morris-Natschke、Kuo-Hsiung Lee

  DOI：10.1021/jm950247k

  日期：1996.1.1

  derivatives of the lead structure, 1-ethyl-2-methylnaphth[2,3-d]imidazole-4,9-dione (5). Their cytotoxic activity in the National Cancer Institute's in vitro cancer cell line panel is reported. In general, substitution of various alkyl, phenyl, or benzyl moieties did not improve activity, and compound 5 remains the most active naphth[2,3-d]imidazole-4,9-dione derivative. However, high levels of activity

  在继续寻找对缓慢生长的实体瘤具有选择性的潜在抗癌药物候选药物的过程中，我们合成了一系列铅结构的1-乙基和2-取代衍生物，即1-乙基-2-甲基萘[2,3-]。 d]咪唑-4，9-二酮（5）。据报道，它们在美国国家癌症研究所的体外癌细胞系中具有细胞毒活性。通常，各种烷基，苯基或苄基部分的取代不会提高活性，并且化合物5仍然是活性最高的萘并[2,3-d]咪唑-4,9-二酮衍生物。但是，发现几种相关的2-（酰基氨基）-3-氯-1,4-萘醌（2f-j）具有较高的活性和选择性。化合物2i，2-[（（2-氟苯基）乙酰胺基] -3-氯-1,4-萘醌，
• METHODS FOR TREATING LEISHMANIASIS
  申请人：HOWARD UNIVERSITY

  公开号：US20140336187A1

  公开（公告）日：2014-11-13

  Methods are provided to inhibit proliferation of Leishmania parasites, and in particular Leshmania donovani with imido-substituted 1,4-naphthoquinones, including novel compounds. Administering an imido-substituted 1,4-naphthoquinone can used to provide prophylaxis or treatment to a patient in need of treatment against leishmaniasis disease.

  提供了抑制利什曼原虫增殖的方法，特别是使用含亚胺基取代的1,4-萘醌类化合物抑制利什曼原虫的增殖，包括新型化合物。给予亚胺基取代的1,4-萘醌类化合物可以用于为需要治疗利什曼病的患者提供预防或治疗。
• Synthesis and antiplatelet, antiinflammatory, and antiallergic activities of 2-substituted 3-chloro-1,4-naphthoquinone derivatives
  作者：Jin-Cherng Lien、Li-Jiau Huang、Jih-Pyang Wang、Che-Ming Teng、Kuo-Hsiung Lee、Sheng-Chu Kuo

  DOI：10.1016/s0968-0896(97)00133-8

  日期：1997.12

  A series of 2-substituted 3-chloro-1,4-naphthoquinones was synthesized, and the antiplatelet, antiinflammatory, and antiallergic activities of these compounds were evaluated. The structure-activity relationships in this series were also examined. Most of the 2-alkyl/arylcarboxamido derivatives of 3-chloro-1,4-naphthoquinone showed potent activities with similar trends in each of the activities evaluated. (C) 1997 Elsevier Science Ltd.
• Synthesis and MEK1 inhibitory activities of imido-Substituted 2-chloro-1,4-naphthoquinones
  作者：Oladapo Bakare、Curtis L. Ashendel、Hairuo Peng、Leon H. Zalkow、Edward M. Burgess

  DOI：10.1016/s0968-0896(03)00267-0

  日期：2003.7

  Mitogen activated protein kinases are of interest as research tools and as therapeutic target for certain physiological disorders. In this study, we found 2-chloro-3-(N-succinimidyl)-1,4-naphthoquinone 6 to be a selective inhibitor of MEK1 with an IC50 of 0.38 muM. An open-chain homologue, 10, showed selective cytotoxicity against renal cancer in the NCI in vitro tumor screeninQ. Structure-activity relationship study of eight compounds showed the cyclic imido-substituted chloro-1,4-naphthoquinone as more potent and selective MEK1 inhibitors than the open chain homologues. The imido-substituted chloro-1,4-naphthoquinones were synthesized in a straightforward fashion by refluxing 2-amino-3-chloro-1,4-naphthoquinone with the appropriate acid chloride or diacyl dichloride. (C) 2003 Elsevier Science Ltd. All rights reserved.
• LITVIN B. L.; KOLESNIKOV V. T., ZH. ORGAN. XIMII, 22,(1986) N 8, 1736-1742
  作者：LITVIN B. L.、 KOLESNIKOV V. T.

  DOI：——

  日期：——