nor-α-lapachone | 52436-87-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: nor-α-lapachone
• 英文别名: 2,3-dihydro-2,2-dimethylnaphtho[2,3-b]furan-4,9-dione；Nor-alpha-lapachone；2,2-dimethyl-3H-benzo[f][1]benzofuran-4,9-dione
• CAS: 52436-87-0
• 化学式: C₁₄H₁₂O₃
• 分子量: 228.247
• InChiKey: MUWYRFXIYYYJTM-UHFFFAOYSA-N

物化性质

• 熔点：
  183-184 °C
• 沸点：
  358.0±42.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  nor-α-lapachone 在 N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 二氯甲烷 、 水 为溶剂， 生成 2,2-dimethyl-3-(4-phenyl-1H-1,2,3-triazol-1-yl)-2,3-dihydronaphtho[2,3-b]furan-4,9-dione
  参考文献：
  名称：

  Synthesis and anti-Trypanosoma cruzi activity of naphthoquinone-containing triazoles: Electrochemical studies on the effects of the quinoidal moiety

  摘要：

  In our continued search for novel trypanocidal compounds, twenty-six derivatives of para-and orthonaphthoquinones coupled to 1,2,3-triazoles were synthesized. These compounds were evaluated against the infective bloodstream form of Trypanosoma cruzi, the etiological agent of Chagas disease. Compounds 17-24, 28-30 and 36-38 are described herein for the first time. Three of these novel compounds (28-30) were found to be more potent than the standard drug benznidazole, with IC50/24 h values between 6.8 and 80.8 mu M. Analysis of the toxicity to heart muscle cells led to LC50/24 h of <125, 63.1 and 281.6 mu M for 28, 29 and 30, respectively. Displaying a selectivity index of 34.3, compound 30 will be further evaluated in vivo. The electrochemical properties of selected compounds were evaluated in an attempt to find correlations with trypanocidal activity, and it was observed that more electrophilic quinones were generally more potent. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.08.055
• 作为产物：
  描述：

  4-hydroxy-3-(2-hydroxy-2-methylpropyl)naphthalene-1,2-dione 在 盐酸 作用下， 生成 nor-α-lapachone
  参考文献：
  名称：

  On the Oxidation of 2-Hydroxy-1,4-naphthoquinone Derivatives with Alkaline Potassium Permanganate^1,2

  摘要：

  DOI：

  10.1021/ja01298a030

文献信息

• Potent antitumor activity of synthetic 1,2-Naphthoquinones and 1,4-Naphthoquinones
  作者：Ngampong Kongkathip、Boonsong Kongkathip、Pongpun Siripong、Chak Sangma、Suwaporn Luangkamin、Momad Niyomdecha、Suppachai Pattanapa、Suratsawadee Piyaviriyagul、Palangpon Kongsaeree

  DOI：10.1016/s0968-0896(03)00226-8

  日期：2003.7

  Rhinacanthone (1) and two 1,2-pyranonaphthoquinones (2,3) were synthesized and found to show very potent cytotoxicity against three cancer cell lines (KB, HeLa and HepG(2)) with IC(50) values of 0.92-9.63 microM, whereas the corresponding hydroxylated derivative 4 had reduced cytotoxicity (IC(50) values of 7.61-24.13 microM). Three 1,2-furanonaphthoquinone derivatives (5-7) were also synthesized with

  合成了Rhinacanthone（1）和两个1,2-吡喃并萘醌（2,3），发现它们对三种癌细胞系（KB，HeLa和HepG（2））具有很强的细胞毒性，IC（50）值为0.92-9.63 microM，而相应的羟基化衍生物4则降低了细胞毒性（IC（50）值为7.61-24.13 microM）。还合成了三种具有与1,2-吡喃萘甲醌相似的细胞毒性的1,2-呋喃萘甲醌衍生物（5-7）。与1,2-萘醌相比，合成了与吡喃环（8-10）和呋喃环（11-13）融合的六个1,4-萘醌衍生物，它们显示出较低的细胞毒性或对癌细胞系无活性。此外，化合物13对HeLa细胞系具有明显的细胞毒性（IC（50）值为9.25 microM），而对Vero细胞无毒性。
• Synthesis and antitumor activity of selenium-containing quinone-based triazoles possessing two redox centres, and their mechanistic insights
  作者：Eduardo H.G. da Cruz、Molly A. Silvers、Guilherme A.M. Jardim、Jarbas M. Resende、Bruno C. Cavalcanti、Igor S. Bomfim、Claudia Pessoa、Carlos A. de Simone、Giancarlo V. Botteselle、Antonio L. Braga、Divya K. Nair、Irishi N.N. Namboothiri、David A. Boothman、Eufrânio N. da Silva Júnior

  DOI：10.1016/j.ejmech.2016.06.019

  日期：2016.10

  Selenium-containing quinone-based 1,2,3-triazoles were synthesized using click chemistry, the copper catalyzed azide-alkyne 1,3-dipolar cycloaddition, and evaluated against six types of cancer cell lines: HL-60 (human promyelocytic leukemia cells), HCT-116 (human colon carcinoma cells), PC3 (human prostate cells), SF295 (human glioblastoma cells), MDA-MB-435 (melanoma cells) and OVCAR-8 (human ovarian

  使用点击化学（铜催化叠氮化物-炔烃 1,3-偶极环加成）合成含硒醌基 1,2,3-三唑，并针对六种类型的癌细胞系进行评估：HL-60（人早幼粒细胞白血病细胞） ）、HCT-116（人结肠癌细胞）、PC3（人前列腺细胞）、SF295（人胶质母细胞瘤细胞）、MDA-MB-435（黑色素瘤细胞）和OVCAR-8（人卵巢癌细胞）。一些化合物显示 IC 50值 < 0.3 μM。还使用非肿瘤细胞（例如外周血单核（PBMC）、V79 和 L929 细胞）测定了所评估的醌的细胞毒性潜力。NAD(P)H:醌氧化还原酶 1 (NQO1) 的机制作用也得到了阐明。这些化合物可以为更有效的抗癌药物开发和递送提供有前途的新先导衍生物，并且代表了报道的最活跃的拉帕酮类之一。
• Synthesis, Stability Studies, and Antifungal Evaluation of Substituted α- and β-2,3-Dihydrofuranaphthoquinones against Sporothrix brasiliensis and Sporothrix schenckii
  作者：Patricia Garcia Ferreira、Luana Pereira Borba-Santos、Leticia Noronha、Caroline Deckman Nicoletti、Marcella de Sá Haddad Queiroz、Fernando de Carvalho da Silva、Sônia Rozental、Débora Omena Futuro、Vitor Francisco Ferreira

  DOI：10.3390/molecules24050930

  日期：——

  standard antifungal itraconazole has been recommended as a first-line therapy. However, failure cases in human and feline treatment have been reported in recent years. This study aimed to synthesize several α- and β-2,3-dihydrofuranaphthoquinones and evaluate them against Sporothrix schenckii and Sporothrix brasiliensis-the main etiological agents of sporotrichosis in Brazil. The stability of these compounds

  孢子丝菌病是由孢子丝菌（Sporothrix spp。）引起的被忽略的真菌感染，其在世界范围内分布。标准抗真菌伊曲康唑已被推荐作为一线治疗药物。然而，近年来已经报道了人类和猫治疗失败的案例。这项研究旨在合成几种α-和β-2,3-二氢呋喃萘醌，并评估它们对巴西孢子虫病的主要病原体-申氏孢子虫和巴西孢子菌的抵抗力。还研究了这些化合物在不同储存条件下3个月的稳定性。在0、60和90天取出样品并通过1 H-NMR评估，并测试其体外抗真菌药敏性。此外，我们使用扫描电子显微镜评估了最有效和稳定的化合物引起的表面变化，并确定了与伊曲康唑合用时的效果。九种二氢呋喃萘醌具有良好的抗真菌活性和稳定性，MIC值为2⁻32µM。对于这两种物种，化合物6和10是体外活性最高的二氢呋喃萘醌。在真菌中，这些化合物诱导了酵母菌丝的转化以及菌丝和分生孢子结构的改变。化合物10还显示出与伊曲康唑对申氏链球菌的协同活性，ΣFIC指数值为0
• Design of hybrid molecules as antimycobacterial compounds: Synthesis of isoniazid-naphthoquinone derivatives and their activity against susceptible and resistant strains of Mycobacterium tuberculosis
  作者：Wallace J. Reis、Ícaro A.O. Bozzi、Matheus F. Ribeiro、Priscila C.B. Halicki、Laís A. Ferreira、Pedro E. Almeida da Silva、Daniela F. Ramos、Carlos A. de Simone、Eufrânio N. da Silva Júnior

  DOI：10.1016/j.bmc.2019.07.045

  日期：2019.9

  C(−5)T) strains. Compounds 1a, 2a, and 8a were effective against the INHR1 strain, and compounds 1a, 1b, 2a, 3a, 5a, 5b and 8a were effective against the INHR2 strain, with MICs in the range of 3.12–6.25 µg/mL. Compounds 1b and 5b were the most active against H37Rv, with MIC of 0.78 µg/mL. Based on the selectivity index, 1b and 5b can be considered safe as a drug candidate compounds. These results demonstrate

  合成异烟肼-萘醌杂种并针对结核分枝杆菌的易感性菌株（H 37 Rv）和两个耐异烟肼菌株（INH R1和INH R2）进行评估。根据刃天青微量滴定法及其在粘附的小鼠单核巨噬细胞J774.A1细胞（ATCC TIB-67）中的细胞毒性，确定了衍生物的抗分枝杆菌活性。在针对三种结核分枝杆菌的评估的22种化合物中，有21种对H 37 Rv和INH R1（katG S315T）或INH R2（inhA C（-5）T）菌株具有一定的活性。化合物1a，2a和8a对INH R1菌株有效，化合物1a，1b，2a，3a，5a，5b和8a对INH R2菌株有效，MIC范围为3.12–6.25 µg / mL。化合物1b和5b对H 37 Rv的活性最高，MIC为0.78 µg / mL。基于选择性指数1b和5b可以被认为是安全的候选药物化合物。这些结果表明，喹诺酮类化合物可用作开发新的抗结核病药物和对结核分枝杆菌
• Naphthoquinone-based chalcone hybrids and derivatives: synthesis and potent activity against cancer cell lines
  作者：Guilherme A. M. Jardim、Tiago T. Guimarães、Maria do Carmo F. R. Pinto、Bruno C. Cavalcanti、Kaio M. de Farias、Claudia Pessoa、Claudia C. Gatto、Divya K. Nair、Irishi N. N. Namboothiri、Eufrânio N. da Silva Júnior

  DOI：10.1039/c4md00371c

  日期：——

  Naphthoquinone-based chalcone hybrids were synthesized and evaluated for their cytotoxic activity against four cancer cell lines and PBMC. Some of the hybrids exhibited promising anticancer activity with IC₅₀ values < 1 μM.

  基于萘醌的查尔酮杂合物被合成并对其对四种癌细胞系和PBMC的细胞毒活性进行了评估。其中一些杂合物表现出有前景的抗癌活性，IC₅₀值小于1μM。