Article
Chemistry, Organic
Yuta Takemasa, Kyoko Nozaki
Summary: In this study, a molecule with both BQ and HQ moieties in a triptycene framework was reported, and two types of crystals with different hydrogen-bonding structures were obtained by changing the cosolvents.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Ying Jin, Zixuan Wang, Nuerbiye Aobulikasimu, Yixuan Hu, Zengguang Zhang, Hang Lv, Yu Mu, Yi Jiang, Li Han, Xueshi Huang
Summary: Four isoquinolinequinones were isolated from lichens-derived Streptomyces albidoflavus. A new isoquinolinequinone, named mansouramycin H, was identified and showed broad cytotoxic activities against MDA-MB-231 cells. The total synthesis of mansouramycin H and its derivatives revealed that the introduction of piperazine moieties improved the activities. Compound 1g exhibited the strongest cytotoxicity and induced apoptosis and cell cycle arrest in MBA-MB-231 cells.
Article
Chemistry, Organic
Joaquim A. M. Castro, Bruno K. Serikava, Christian R. S. Maior, Fabricio F. Naciuk, Silvana A. Rocco, Carolina B. P. Ligiero, Nelson H. Morgon, Paulo C. M. L. Miranda
Summary: Ellipticine was synthesized from 2,5-dimethoxyisoquinoline in six steps with a 20% global yield. The regioselective control of nucleophilic attack on isoquinoline-5,8-dione is described for the first time. Density functional theory calculations revealed the unexpected role of N-oxide in cascade tautomerizations and nucleophilic attack, accelerating the overall process.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Biochemistry & Molecular Biology
Diego Caprioglio, Daiana Mattoteia, Orazio Taglialatela-Scafati, Eduardo Munoz, Giovanni Appendino
Summary: Neutral cannabinoids can be converted into quinone derivatives by oxidative dearomatization, but stability issues have hindered cannabinoquinone research. Full substitution of the quinone ring and introduction of steric hindrance on the alkyl substituent have led to the discovery of a promising compound, VCE-004.8, under phase 2 clinical development for the management of scleroderma. Further exploration of the synthesis and chemistry of these compounds will help unlock their full biological profile and clinical potential.
Article
Chemistry, Organic
Yusuke Akagi, Kohei Harasawa, Toshiya Komatsu
Summary: The total synthesis of phenanthroviridin aglycon with interesting antibacterial and anticancer activities was reported in this study. The synthesis involved a Pd-catalyzed direct arylation of 5-hydroxy-1,4-naphthoquinone with aryl iodides prepared from 3,5-dimethylphenol, followed by treatment with aqueous ammonia, oxidative cyclization, and deprotection to yield the target compounds.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Chang-Qiu Guo, Chuan-Jun Lu, Li-Wen Zhan, Peng Zhang, Qi Xu, Jia Feng, Ren-Rong Liu
Summary: This study reports a new catalyst that successfully catalyzes the enantioselective coupling reaction between quinone esters and anilines, resulting in the formation of N-aryl quinone atropisomers with a unique intramolecular hydrogen bond. This method has the potential to be used for the synthesis of structurally diverse secondary amine atropisomers.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Swamy Peraka, Badaraita Gorachand, Akram Hussain, Revoju Sravanthi, Dhevalapally B. Ramachary
Summary: Structurally complex cedrane scaffolds were synthesized in high yields and selectivities using a sequential one-pot method. This green synthesis approach demonstrates the unique combination of coupling and annulation routes, with the highlight on organocatalytic ring isomerization.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Soumyadip Hore, Abhijeet Singh, Shreemoyee De, Neetu Singh, Vincent Gandon, Ravi P. Singh
Summary: In this study, a new method for synthesizing polyarylquinones using palladium-catalyzed dehydrogenative cycloaddition reaction was reported. High regioselectivity was achieved by precisely controlling the addition of fulvene moieties onto quinones, and the mechanism and substrate scope of the reaction were explored. Additionally, single-crystal X-ray diffraction revealed the potential application of these materials in optoelectronics. The synthesized polyarylquinones were screened for their redox properties and found to exhibit excellent antioxidant and chemotherapeutic properties.
Article
Chemistry, Medicinal
Yong Wang, Pascal Pigeon, Wei Li, Jiangkun Yan, Patrick M. Dansette, Mohamed Othman, Michael J. McGlinchey, Gerard Jaouen
Summary: Ferrociphenols, compounds characterized by a biologically active redox motif, have anticancer properties. This study synthesized a variety of ferrociphenols with nitrogen-containing substituents and investigated their structure-activity relationships. Oxidative metabolism experiments and ROS-related bioactivity measurements were conducted to explore the cytotoxicity of imidoferrociphenols. Additionally, dimerization phenomenon observed in the crystal structure of a ferrociphenol may affect its antitumor activity.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Review
Chemistry, Organic
Carolina G. S. Lima, Acacio S. de Souza, Fernanda P. Pauli, Ruan Carlos B. Ribeiro, Amanda de A. Borges, Patricia G. Ferreira, Fernando de C. da Silva, Vitor F. Ferreira, Luana da S. M. Forezi
Summary: This review provides insights into the chemistry, chemical synthesis, semi-synthesis, pharmacological effects, and reactivity of low molecular weight mono-and bis(aminonaphthoquinones). It discusses the importance of functional groups linked to the 1,4-naphthoquinone scaffold and the introduction of nitrogen containing groups into this nucleus for amplifying its biological activity. Additionally, the review examines the use of important 1,4-naphthoquinones as starting materials for the synthesis of amino-1,4-naphthoquinones, the modification of ANQ derivatives, and future outlooks in this field.
CURRENT ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Luana S. Gomes, Erica O. Costa, Thuany G. Duarte, Mateus H. Kohler, Bruna M. Rodrigues, Vitor F. Ferreira, Fernando de C. da Silva, Bernardo A. Iglesias, Vanessa Nascimento
Summary: This study presents a comprehensive analysis of a novel series of chalcogen-naphthoquinone-1,2,3-triazole hybrids, including their synthesis, structural elucidation, photophysical behavior, and electrochemical properties. These hybrids were synthesized with remarkable efficiency and exhibit exceptional photophysical and electrochemical properties, promising potential applications in biological assays.
Article
Chemistry, Multidisciplinary
Subramaniyan Prasanna Kumari, Savarimuthu Philip Anthony, Subramaniapillai Selva Ganesan
Summary: A convenient one-pot, two-step methodology has been developed to transform readily available planar naphthoquinone derivatives into structurally complex indole-fused nitrogen heterocycles under aerobic conditions. The structural design in the synthetic protocols offered an opportunity to obtain deep red emitting solid-state fluorescence materials. Mechanistic studies revealed the crucial role of atmospheric oxygen in the transformation.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Sobi Asako, Takafumi Kobayashi, Seina Ishihara, Kazuhiko Takai
Summary: A simple catalytic system composed of Mo(0) and ortho-quinone as catalyst, and phosphine as a reductant, has been developed for the synthesis of pyridoisoindoles and pyridoisoindolium salts through deoxygenation of carbonyl compounds.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Marco Buccini, Louisa Tham, Francis Dhoro, Brian W. Skelton, Craig M. Williams, Matthew J. Piggott
Summary: The study attempted to synthesize the marine natural product alpkinidine using model chemistry, but faced challenges in certain reactions, preventing the direct synthesis of the target product.
Article
Chemistry, Organic
Dongwei Wang, Zuosen Shi, Xueyou Zhang, Zhanchen Cui, Qifeng Wang
Summary: A novel pathway for oxidation of 9-phenanthrenol was reported, yielding an unprecedented ketal structure. The ketal can be utilized as a substrate to synthesize 9-fluorenone and its derivatives in good to high yields with good functional group tolerance. Decomposition and formation processes of the ketal were also investigated.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Biochemistry & Molecular Biology
Christopher R. Anderton, Kaiyan Lou, Peter K. Weber, Ian D. Hutcheon, Mary L. Kraft
BIOCHIMICA ET BIOPHYSICA ACTA-BIOMEMBRANES
(2011)
Article
Biochemistry & Molecular Biology
Duy H. Hua, Huiping Zhao, Srinivas K. Battina, Kaiyan Lou, Ana L. Jimenez, John Desper, Elisabeth M. Perchellet, Jean-Pierre H. Perchellet, Peter K. Chiang
BIOORGANIC & MEDICINAL CHEMISTRY
(2008)
Article
Chemistry, Multidisciplinary
Vahid Mirshafiee, Morteza Mahmoudi, Kaiyan Lou, Jianjun Cheng, Mary L. Kraft
CHEMICAL COMMUNICATIONS
(2013)
Article
Pharmacology & Pharmacy
Zeting Yuan, Yajing Ye, Feng Gao, Huihui Yuan, Minbo Lan, Kaiyan Lou, Wei Wang
INTERNATIONAL JOURNAL OF PHARMACEUTICS
(2013)
Article
Biochemistry & Molecular Biology
Raehyun Kim, Kaiyan Lou, Mary L. Kraft
JOURNAL OF LIPID RESEARCH
(2013)
Article
Multidisciplinary Sciences
Jessica F. Frisz, Kaiyan Lou, Haley A. Klitzing, William P. Hanafin, Vladimir Lizunov, Robert L. Wilson, Kevin J. Carpenter, Raehyun Kim, Ian D. Hutcheon, Joshua Zimmerberg, Peter K. Weber, Mary L. Kraft
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
(2013)
Article
Chemistry, Physical
Christopher R. Anderton, Bita Vaezian, Kaiyan Lou, Jessica F. Frisz, Mary L. Kraft
SURFACE AND INTERFACE ANALYSIS
(2012)
Meeting Abstract
Biochemistry & Molecular Biology
Mary L. Kraft, Haley A. Klitzing, Kaiyan Lou, Joshua Zimmerberg, Peter K. Weber
Meeting Abstract
Biochemistry & Molecular Biology
Mary L. Kraft, Jessica F. Frisz, Haley A. Klitzing, Kaiyan Lou, Vladimir Lizunov, Joshua Zimmerberg, Peter K. Weber
Meeting Abstract
Biophysics
Mary L. Kraft, Jessica F. Frisz, Kaiyan Lou, William Hanafin, Peter K. Weber, Kevin J. Carpenter, Joshua Zimmerberg, Ian D. Hutcheon
BIOPHYSICAL JOURNAL
(2011)
Meeting Abstract
Chemistry, Multidisciplinary
Mary L. Kraft, Kaiyan Lou, Jessica F. Frisz, Peter K. Weber, Kevin J. Carpenter, William P. Hanafin, Ian D. Hutcheon
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY
(2010)
Article
Oncology
Elisabeth M. Perchellet, Yang Wang, Kaiyan Lou, Huiping Zha, Srinivas K. Battina, Duy H. Hua, Jean-Pierre H. Perchellet
INTERNATIONAL JOURNAL OF ONCOLOGY
(2007)
Article
Oncology
Elisabeth M. Perchellet, Yang Wang, Kaiyan Lou, Huiping Zhao, Srinivas K. Battina, Duy H. Hua, Jean-Pierre H. Perchellet
ANTICANCER RESEARCH
(2007)
Article
Pharmacology & Pharmacy
Taro Yamada, Junichi Komoto, Kaiyan Lou, Akiharu Ueki, Duy H. Hua, Kimio Sugiyama, Yoshimi Takata, Hirofumi Ogawa, Fusao Takusagawa
BIOCHEMICAL PHARMACOLOGY
(2007)