Article
Chemistry, Organic
Jantra Jantrapirom, Nitwaree Palavong, Jumreang Tummatorn, Charnsak Thongsornkleeb, Somsak Ruchirawat
Summary: Our research develops a divergent synthesis approach for the production of 3,4-dihydro-2H-benzo[h]chromen-2-one and fluorenone derivatives using ortho-alkynylarylketones as common precursors. The synthesis of 3,4-dihydro-2H-benzo[h]chromen-2-ones involves silver catalyzed ketonization, double intramolecular cyclization, and decarboxylation, while the preparation of fluorenone derivatives proceeds through the formation of indenone analogs and subsequent intramolecular cyclization.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Dehe Wang, Lingyu Zhao, Yongjun Zhang, Ye Zhang, Xianqiang Huang, Guodong Shen
Summary: In this study, economic and practical strategies were developed to synthesize 3-benzyl-/3-benzyl-2-phenyl-benzo[4,5]imidazo[2,1-b]thiazoles via direct nucleophilic attack/addition cyclization and C-H bond activation reactions. The optimized reaction conditions allowed for the tolerance of various electron-donating and electron-withdrawing groups, resulting in new benzo[4,5]imidazo[2,1-b]thiazoles with good to excellent yields (up to 93% yield).
Article
Biochemistry & Molecular Biology
Srinivas Gali, D. Raghu, Veerabhadraiah Mallikanti, Vishnu Thumma, Namratha Vaddiraju
Summary: A series of novel 3-(1H-benzo[d]imidazol-2-yl)-3,4-dihydro-2H-benzo[ e][1,3] oxazine analogues were synthesized using a two-step synthetic protocol. The compound structures were determined through interpretation of H-1 NMR, C-13 NMR, and Mass spectral data after purification. In vitro anti-cancer screening against breast cancer cell lines MCF 7 and MDA-MB-231 showed that compound 4e displayed superior activity with -IC50 values of 8.60 +/- 0.75 and 6.30 +/- 0.54 mu M, compared to Doxorubicin. Compound 4g also demonstrated excellent activity with an -IC50 value of 8.52 +/- 0.62 mu M against the MDA-MB-231 cell line. Docking studies indicated that all compounds had strong binding affinities towards EGFR, making them potential therapeutic agents.
MOLECULAR DIVERSITY
(2023)
Article
Chemistry, Physical
Debjyoti Pal, Avijit Mondal, Dipankar Srimani
Summary: The synthesis of N-heterocycles is an emerging topic in chemical research, with wide applications in medicinal chemistry, materials science, and natural product synthesis. Developing green and sustainable strategies using readily available renewable starting materials is a high priority for the scientific community. In this study, the authors described the first Mn-catalyzed synthesis of quinazoline-4(3H)-ones and 3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxides via acceptorless dehydrogenative annulation. This method shows promise in the efficient construction of intermediate compounds for luotonins A, B, and E.
CATALYSIS SCIENCE & TECHNOLOGY
(2022)
Article
Chemistry, Inorganic & Nuclear
Zahra Dehbanipour, Ali Zarnegareyan
Summary: This study investigates the synthesis and characterization of a new heterogeneous catalyst, Pd(II)Cl2-BTP@MNPs, which is composed of palladium (II) 3,5-bis(2-benzothiazolyl)pyridine supported on magnetic nanoparticles. The catalyst shows excellent performance in the reaction between derivatives of benzyl alcohol with 1,2-phenylenediamine or 2-aminothiophenol, leading to the synthesis of benzothiazoles and benzimidazoles. Furthermore, the catalyst can be reused multiple times without significant loss of catalytic activity.
INORGANIC CHEMISTRY COMMUNICATIONS
(2022)
Article
Chemistry, Physical
Hala E. M. Tolan, Asmaa M. Fahim, Eman H. I. Ismael
Summary: In this study, different 1,3,4-oxadiazoles, 1,2,4-triazoles, and 1,2,4-triazolo[3,4-b]1,3,4-thiadiazine ring system were synthesized through the reaction of hydrazide derivatives with CS 2 in ethanolic potassium hydroxide, followed by acidification with HCl. The synthesized compounds exhibited anti-tumor activity against HepG2 and MCF-7 cell lines, and the results were confirmed through docking simulation with PDBID: 4hqd and PDBID: 5h38.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Organic
Thuy Quynh Le, Chang Ho Oh
Summary: An efficient and facile method utilizing PTSA catalyst has been developed for the synthesis of 2,3-dihydronaphtho[2,3-b]furan and 3,4-dihydro-2H-benzo[g]chromene. This methodology shows high yield cyclization reaction of ortho-oxalate-, ortho-keto-, and ortho-formyl arylacetylenols. It is also successfully applied to the large-scale synthesis of the naphthofuran skeleton.
SYNTHETIC COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Xuetong Li, Jordi Benet-Buchholz, Eduardo C. Escudero-Adan, Arjan W. Kleij
Summary: A conceptually novel catalytic domino approach is presented for the synthesis of highly functional 1,4-dihydro-2H-1,3-benzoxazine-2-one derivatives. The chemoselectivity is achieved through a proper design of the precursor and the use of Thorpe-Ingold effects. The synthetic diversity of these CO2-based heterocycles is demonstrated, and an unusual ring-expansion sequence is observed from an alpha-alkylidene, five-membered cyclic carbonate to a six-membered cyclic carbamate by N-induced isomerization.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Viraj A. Bhosale, Martin Nigrini, Martin Dracinsky, Ivana Cisarova, Jan Vesely
Summary: The study presents a versatile method for the synthesis of chiral 2H-1,4-benzoxazines using chiral phosphoric acid catalysis, achieving high yields and enantioselectivity under mild conditions. This strategy expands on traditional methods and provides access to key intermediates for therapeutic candidates, such as prostaglandin D2 receptor antagonists and MI positive allosteric modulator (PAM) compound VU0486846.
Article
Chemistry, Organic
Bharat Singh, Manish Kumar, Gaurav Goswami, Indresh Verma, Manas K. Ghorai
Summary: Activated aziridines react with propargyl alcohols in the presence of Zn(OTf)2 as the catalyst to form amino ether derivatives. These derivatives undergo intramolecular hydroamination via 6-exo-dig cyclization under one-pot two-step reaction conditions using Zn(OTf)2 as the catalyst and tetrabutylammonium triflate salt as an additive. However, for nonracemic examples, the reaction requires two-pot conditions. The reaction shows good efficiency without the need for additional solvents, yielding 3,4-dihydro-2H-1,4-oxazine products with 13 to 84% yield and 78 to 98% enantiomeric excess (for nonracemic examples).
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Bharat Singh, Manish Kumar, Gaurav Goswami, Indresh Verma, Manas K. Ghorai
Summary: Activated aziridines reacted with propargyl alcohols under the catalysis of Zn(OTf)2, following an SN2-type ring-opening mechanism to produce amino ether derivatives. These amino ethers underwent intramolecular hydroamination via 6-exo-dig cyclization in the presence of Zn(OTf)2 as the catalyst and tetrabutylammonium triflate salt as an additive under one-pot two-step reaction conditions. However, for nonracemic examples, ring-opening and cyclization steps were conducted separately. The reaction proceeded well without the need for additional solvents, yielding 3,4-dihydro-2H-1,4-oxazine products with 13 to 84% yield and 78 to 98% enantiomeric excess (for nonracemic examples).
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Zhengjie Le, Yiwen Zhu, Zhi-Peng Bao, Jun Ying, Xiao-Feng Wu
Summary: A new palladium-catalyzed reaction has been developed for the efficient synthesis of 1,5-dihydro-2H-pyrrol-2-ones using benzene-1,3,5-triyl triformate as the CO source.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Barbara Klausfelder, Patricia Blach, Niels de Jonge, Rhett Kempe
Summary: This study reports a method for the synthesis of 3,4-dihydro-2H-pyrroles via the hydrogenation and cyclization of nitro ketones. The use of inexpensive and readily available starting materials allows for the flexible introduction of various substitution patterns. The reaction shows a broad scope and 23 out of the 33 synthesized compounds are previously unreported.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Physical
Koffi Senam Etse, Guillermo Zaragoza, Kodjo Djidjole Etse
Summary: This study synthesized and characterized a new 3,3-dimethyl-substituted 1,2,4-benzothiadiazine 1,1-dioxide, and suggested its potential as a lead-like drug through various analyses. Molecular docking results indicated that the compound could interact with the AMPAR and be a positive allosteric modulator, showing potential therapeutic value.
JOURNAL OF MOLECULAR STRUCTURE
(2021)
Article
Chemistry, Organic
Sho Amemiya, Yui Takahashi, Akira Tsubouchi, Akio Saito
Summary: By controlling the conditions, 3-acylpyrrolidines can be synthesized and further subjected to a domino reaction to afford the desired product 4-alkylidene-3,4-dihydro-2H-pyrroles.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Pharmacology & Pharmacy
Natasha Jaiswal, Naresh Gunaganti, Chandan Kumar Maurya, Tadigoppula Narender, Akhilesh Kumar Tamrakar
EUROPEAN JOURNAL OF PHARMACOLOGY
(2015)
Article
Chemistry, Organic
Gunaganti Naresh, Ruchir Kant, Tadigoppula Narender
Article
Chemistry, Organic
Brendan Frett, Nicholas McConnell, Anupreet Kharbanda, Gunaganti Naresh, Benjamin Rounseville, Christina Warner, John Chang, Natalie Debolske, Hong-yu Li
Article
Multidisciplinary Sciences
Jaideep B. Bharate, Nicholas McConnell, Gunaganti Naresh, Lingtian Zhang, Naga Rajiv Lakkaniga, Lucky Ding, Neil P. Shah, Brendan Frett, Hong-yu Li
SCIENTIFIC REPORTS
(2018)
Article
Chemistry, Medicinal
Wei Yan, Naga Rajiv Lakkaniga, Francesca Carlomagno, Massimo Santoro, Neil Q. McDonald, Fengping Lv, Naresh Gunaganti, Brendan Frett, Hong-yu Li
JOURNAL OF MEDICINAL CHEMISTRY
(2019)
Article
Chemistry, Organic
Gunaganti Naresh, Naga Rajiv Lakkaniga, Anupreet Kharbanda, Wei Yan, Brendan Frett, Hong-yu Li
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Meeting Abstract
Oncology
Jorge Contreras, Eloisi Caldas-Lopes, David Jayabalan, Jorge Monge, Nicholas Lombardi, Hong-yu Li, Naresh Gunaganti, Ruben Niesvizky, Monica Guzman
CLINICAL LYMPHOMA MYELOMA & LEUKEMIA
(2019)
Article
Chemistry, Medicinal
Pragya Chandrakar, Naresh Gunaganti, Naveen Parmar, Ashok Kumar, Sandeep Kumar Singh, Mamunur Rashid, M. Wahajuddin, Kalyan Mitra, Tadigopula Narender, Susanta Kar
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2019)
Article
Chemistry, Medicinal
Naga Rajiv Lakkaniga, Naresh Gunaganti, Lingtian Zhang, Binyam Belachew, Brendan Frett, Yuet-Kin Leung, Hong-yu Li
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2020)
Article
Chemistry, Medicinal
Baljinder Singh, Rosario Diaz-Gonzalez, Gloria Ceballos-Perez, Domingo I. Rojas-Barros, Naresh Gunaganti, Kirsten Gillingwater, Maria Santos Martinez-Martinez, Pilar Manzano, Miguel Navarro, Michael P. Pollastri
JOURNAL OF MEDICINAL CHEMISTRY
(2020)
Article
Chemistry, Medicinal
Naga Rajiv Lakkaniga, Lingtian Zhang, Binyam Belachew, Naresh Gunaganti, Brendan Frett, Hong-yu Li
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2020)
Correction
Chemistry, Medicinal
Wei Yan, Naga Rajiv Lakkaniga, Francesca Carlomagno, Massimo Santoro, Neil Q. McDonald, Fengping Lv, Naresh Gunaganti, Brendan Frett, Hong-yu Li
JOURNAL OF MEDICINAL CHEMISTRY
(2020)
Meeting Abstract
Oncology
Jorge Contreras, Eloisi Caldas Lopes, Jorge Monge, David Jayabalan, Naresh Gunaganti, Brendan Frett, Hong-yu Li, Morton Coleman, Ruben Niesvizky, Monica L. Guzman
Article
Chemistry, Multidisciplinary
Naresh Gunaganti, Anupreet Kharbanda, Naga Rajiv Lakkaniga, Lingtian Zhang, Rose Cooper, Hong-yu Li, Brendan Frett
CHEMICAL COMMUNICATIONS
(2018)