Highly Efficient Synthesis and Structure-Activity Relationships of a Small Library of Substituted 1,4-Naphthoquinones

被引：13

作者：

Bao, Na ^{[1
]}

Ou, Jinfeng ^{[1
]}

Shi, Wei ^{[1
]}

Li, Na ^{[1
]}

Chen, Li ^{[1
]}

Sun, Jianbo ^{[1
]}

机构：

[1] China Pharmaceut Univ, Sch Tradit Chinese Pharm, State Key Lab Nat Med, 24 Tong Jia Xiang, Nanjing 210009, Jiangsu, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 2018卷 / 19期

关键词：

Synthetic methods; Quinones; Cytotoxicity; Structure-activity relationships; PLUMBAGIN; NAPHTHOQUINONES; APOPTOSIS; DROSERONE; JUGLONE;

D O I：

10.1002/ejoc.201800207

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A platform of highly efficient synthetic methodologies has been established to access a focused library of substituted 1,4-naphthoquinones derivatives functionalized with a diversity of amino/hydroxy/alkyl groups. Furthermore, the structure-activity relationship deduced from antiproliferative activities and toxicities of this 1,4-naphthoquinone library and intracellular reactive oxygen species (ROS) level detections might warrant future potential of plumbagin (2) and compound 13 as promising basic structures to develop novel anti-cancer agents.

引用

收藏

页码：2254 / 2258

页数：5

相关论文

共 25 条

[1]

Akhtar Y, 2012, IND CROP PROD, V37, P536, DOI [10.1016/j.indCrop.2011.07.033, 10.1016/j.indcrop.2011.07.033]

[2] Structure/Antileishmanial Activity Relationship Study of Naphthoquinones and Dependency of the Mode of Action on the Substitution Patterns [J].

Ali, Ahmad ;

Assimopoulou, Andreana Nikolaos ;

Papageorgiou, Vassilios Peter ;

Kolodziej, Herbert .

PLANTA MEDICA, 2011, 77 (18) :2003-2012

[3] Mangrove rare actinobacteria: taxonomy, natural compound, and discovery of bioactivity [J].

Azman, Adzzie-Shazleen ;

Othman, Iekhsan ;

Velu, Saraswati S. ;

Chan, Kok-Gan ;

Lee, Learn-Han .

FRONTIERS IN MICROBIOLOGY, 2015, 6

[4] Droserone from cell cultures of Triphyophyllum peltatum (Dioncophyllaceae) and its biosynthetic origin [J].

Bringmann, G ;

Rischer, H ;

Wohlfarth, M ;

Schlauer, J ;

Assi, LA .

PHYTOCHEMISTRY, 2000, 53 (03) :339-343

[5] Cytotoxic action of juglone and plumbagin: A mechanistic study using HaCaT keratinocytes [J].

Inbaraj, JJ ;

Chignell, CF .

CHEMICAL RESEARCH IN TOXICOLOGY, 2004, 17 (01) :55-62

[6] Poly(ADP-ribose) polymerase and the therapeutic effects of its inhibitors [J].

Jagtap, P ;

Szabó, C .

NATURE REVIEWS DRUG DISCOVERY, 2005, 4 (05) :421-440

[7] Combination of Silver Nanoparticles and Drosera binata Extract as a Possible Alternative for Antibiotic Treatment of Burn Wound Infections Caused by Resistant Staphylococcus aureus [J].

Krychowiak, Marta ;

Grinholc, Mariusz ;

Banasiuk, Rafal ;

Krauze-Baranowska, Miroslawa ;

Glod, Daniel ;

Kawiak, Anna ;

Krolicka, Aleksandra .

PLOS ONE, 2014, 9 (12)

[8] Anti-inflammatory and Analgesic Effect of Plumbagin through Inhibition of Nuclear Factor-κB Activation [J].

Luo, Pei ;

Wong, Yuen Fan ;

Ge, Lin ;

Zhang, Zhi Feng ;

Liu, Yuan ;

Liu, Liang ;

Zhou, Hua .

JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, 2010, 335 (03) :735-742

[9] Synthesis of Vitamin K and Related Naphthoquinones via Demethoxycarbonylative Annulations and a Retro-Wittig Rearrangement [J].

Mal, Dipakranjan ;

Ghosh, Ketaki ;

Jana, Supriti .

ORGANIC LETTERS, 2015, 17 (23) :5800-5803

[10] Reactive oxygen species as double-edged swords in cellular processes: low-dose cell signaling versus high-dose toxicity [J].

Martin, KR ;

Barrett, JC .

HUMAN & EXPERIMENTAL TOXICOLOGY, 2002, 21 (02) :71-75