Article
Chemistry, Inorganic & Nuclear
Nishigandha Mone, Shital Harihar, Sunita Salunke-Gawali, Surekha Satpute, Archana Patil, Vivek Mokashi, Mahesh Jadhav, Ray J. Butcher
Summary: The Mn(II), Co(II), Ni(II), Cu(II) and Zn(II) complexes of Henna; 2-hydroxy-1,4-naphthoquinone (Lw) were synthesized and characterized. The composition of all complexes was [M(Lw)(2)(H2O)(2)]. The geometry of the complexes synthesized at 0°C was trans, while cis for complex 4 at 26°C. The crystal structures of copper complexes 4A and its pyridine adduct (4Apy) were determined by single crystal X-ray diffraction studies. The complexes synthesized at 0°C showed enhanced anticancer activity against the A549 cell line. Cell cycle analysis, mitochondrial potential, Reactive Oxygen Species (ROS), peripheral blood mononuclear cells (PBMCs), and Tunnel assay were performed on complex 1A.
INORGANICA CHIMICA ACTA
(2023)
Article
Chemistry, Inorganic & Nuclear
Shital Harihar, Nishigandha Mone, Surekha K. Satpute, Dattatray Chadar, Debamitra Chakravarty, Thomas Weyhermueller, Ray J. Butcher, Sunita Salunke-Gawali
Summary: This study investigated the anticancer activity of phthiocol and its metal complexes against cancer cells, revealing that the metal complexes synthesized at 0 degrees Celsius showed significant cytotoxic effects on breast and lung cancer cell lines, and the impact on peripheral blood mononuclear cells helped evaluate their safety.
DALTON TRANSACTIONS
(2022)
Article
Chemistry, Organic
Bei Wang, Hong Xu, Fu-Yu Li, Ji-Yu Wang
Summary: A divergent transformation of 2-amino-1,4-quinones was developed for the synthesis of pyrroquinone derivatives and 2-halo-3-amino-1,4-quinones. The mechanism study revealed that both the tandem cyclization and halogenation involved Cu(I)-catalyzed oxidative radical processes. This protocol not only fabricated novel pyrroquinone derivatives with high atom economy but also provided a new method for halogenation through directed C(sp(2))-H functionalization, using CuX (X = I, Br, Cl) as the X source.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Pharmacology & Pharmacy
Emerson Lucena da Silva, Felipe Pantoja Mesquita, Ingryd Nayara de Farias Ramos, Carinne Borges de Souza Moraes Rego Gomes, Caroline dos Santos Moreira, Vitor Francisco Ferreira, David Rodrigues da Rocha, Marcelo de Oliveira Bahia, Caroline Aquino Moreira-Nunes, Carolina Rosal Teixeira de Souza, Rommel Mario Rodrigues Burbano, Raquel Carvalho Montenegro
Summary: CNN16 exhibits anticancer effects in colon cancer cells with minimal impact on non-cancerous cells, inducing genotoxicity and reactive oxygen species. Through various experiments and analyses, CNN16 shows inhibition of cancer cells, induction of apoptosis, and inhibition of migration in wound healing assay.
TOXICOLOGY AND APPLIED PHARMACOLOGY
(2022)
Article
Chemistry, Organic
Mayurakhi Bhuyan, Gakul Baishya
Summary: A new method for the synthesis of 2-amino-1,4-naphthoquinones and 1,4-naphthoquinon-2-sulfides from 1,4-naphthoquinone using a Lewis acid catalyst, BiCl3, has been developed. This method has a broad substrate scope and easy product extraction. It is cost-effective, requires mild and sustainable reaction conditions, and provides high product yields. Furthermore, this study presents a novel technique for one-pot sequential amine-arylation using amines and arylhydrazines/K2S2O8 to directly produce arylated 2-amino-1,4-naphthoquinones from 1,4-naphthoquinone, demonstrating the generation of aryl radicals from arylhydrazines and their subsequent free radical coupling reactions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Hua-Yuan Tan, Feng-Ming Liang, Wen-Jing Zhang, Yi Zhang, Jun-Hao Cui, Yu-Yu Dai, Xue-Mei Qiu, Wen-Hang Wang, Yue Zhou, Dan-Ping Chen, Cheng-Peng Li
Summary: A series of 1,4-naphthoquinone derivatives were synthesized and their crystal structure was confirmed. One of the derivatives, compound 5i, showed significant cytotoxicity on the A549 cell line. Further experiments revealed that compound 5i induced autophagy and activated the EGFR signal pathway in A549 cells. Molecular docking study identified the potential binding pattern between compound 5i and EGFR tyrosine kinase. This research opens up possibilities for further studies and development of anti-cancer drugs.
Article
Multidisciplinary Sciences
Rishikesh Patil, Mahesh Jadhav, Sunita Salunke-Gawali, Dipali N. Lande, Shridhar P. Gejji, Debamitra Chakravarty
Summary: In this study, the H-1 and C-13 chemical shifts of 32 compounds of C (3) substituted 2-(n-alkylamino)-3R-naphthalene-1,4-dione were investigated using various NMR experiments and density functional theory. The inter and intra-molecular hydrogen bonding interactions of Br-3 single crystal X-ray structure and 18 different derivatives of naphthalene-1,4-diones were revealed.
Article
Electrochemistry
Andy A. Cardenas-Riojas, Golfer Muedas-Taipe, Adolfo La Rosa-Toro, Maria D. P. T. Sotomayor, Miguel Ponce-Vargas, Angelica M. Baena-Moncada
Summary: An electrochemical sensor based on a glassy carbon electrode modified with 2-hydroxy-1,4-naphthoquinone (HNFQ) has been developed for the detection of the complex ion [Ni(CN)4]2- from galvanic wastewater. The sensor exhibits a wide linear range, excellent selectivity, and sensitivity, and a computational study reveals the molecular interplay between the complex and the graphitic surface of the electrode.
JOURNAL OF APPLIED ELECTROCHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Mingshi Pan, Yixin Tong, Xiaodong Qiu, Xiaobao Zeng, Biao Xiong
Summary: A method for accessing 3-trifluoromethyl-1,4-benzoxazines from CF3-imidoyl sulfoxonium ylides and 2-bromophenols has been demonstrated. This method proceeds through a one-pot two-step sequence involving O-H insertion and annulation, and offers the advantages of a broad substrate scope, excellent functional tolerance, and simplicity of operation.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Medicinal
Sergey A. Dyshlovoy, Dmitry N. Pelageev, Lea S. Jakob, Ksenia L. Borisova, Jessica Hauschild, Tobias Busenbender, Moritz Kaune, Ekaterina A. Khmelevskaya, Markus Graefen, Carsten Bokemeyer, Victor Ph Anufriev, Gunhild von Amsberg
Summary: Synthesized (2-chloroethylthio)-1,4-naphthoquinone derivatives exhibit promising anticancer properties in vitro, suggesting their further development as potential therapeutics for the treatment of castration-resistant prostate cancer.
Article
Chemistry, Medicinal
Renata Maria Costa Souza, Lilian Maria Lapa Montenegro Pimentel, Laryssa Kathleen Mendonca Ferreira, Valeria Rego Alves Pereira, Aline Caroline Da Silva Santos, Willyenne Marilia Dantas, Carla Jasmine Oliveira Silva, Ramayana Morais De Medeiros Brito, Jose Lucas Andrade, Valter Ferreira De Andrade-Neto, Ricardo Toshio Fujiwara, Lilian Lacerda Bueno, Valdemiro Amaro Silva Junior, Lindomar Pena, Celso Amorim Camara, Brijesh Rathi, Ronaldo Nascimento De Oliveira
Summary: This study evaluated the antimalarial activities of 2-amino-1,4-naphthoquinone derivatives (containing 1,2,3-triazole) in both in vitro and in vivo models. The results showed that two compounds exhibited antimalarial activity, suggesting their potential value in drug discovery platform.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Javier Maldonado, Alfonso Oliva, Aurora Molinari, Waldo Acevedo
Summary: A novel series of chalcone-1,4-naphthoquinone/benzohydroquinone compounds were synthesized and evaluated for their antiproliferative activity against breast adenocarcinoma and colorectal carcinoma cells. Some of the compounds exhibited cytotoxicity and showed strong binding to kinase proteins involved in carcinogenic pathways. In silico analysis suggested their potential as candidates for cancer pre-clinical assays.
Article
Chemistry, Applied
Takaaki Aijima, Shinsuke Komagawa, Shuji Akai, Yoshinari Sawama
Summary: In this study, it was found that Siloxy-4-(benzyloxy)methyl-1,4-epoxy-1,4-dihydronaphthalenes can undergo automatic site-selective ring opening and subsequent annulation with olefins to form multi-fused heterocycles. The study also revealed the solvent-dependent regioselectivity in certain reactions.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Plant Sciences
Waldemar Karcz, Zbigniew Burdach, Malgorzata Rudnicka
Summary: This study investigated the effects of 1,4-naphthoquinone (NQ) and naphthazarin (DHNQ) individually and in combination at low concentrations on growth, H2O2 production, catalase activity, and lipid peroxidation in maize seedlings. The results showed that NQ and DHNQ had different effects on the fresh weight of the aboveground and underground parts of the seedlings. NQ and DHNQ also influenced H2O2 production, catalase activity, and lipid peroxidation in a concentration-dependent manner.
Article
Chemistry, Medicinal
Manoj Manickam, Pulla Reddy Boggu, Thanigaimalai Pillaiyar, Yeo Jin Nam, Md. Abdullah, Seung Jin Lee, Jong Seong Kang, Sang-Hun Jung
Summary: A series of potent naphthoquinone amines were synthesized and studied for their anticancer activity, in addition to the development of a tumor targeting drug delivery system using Biotin/polyamine conjugates.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2021)