Article
Chemistry, Multidisciplinary
Nikita M. Chernov, Roman Shutov, Nadezhda Yu Sipkina, Maxim N. Krivchun, Igor P. Yakovlev
Summary: A flexible approach was developed for the synthesis of phenanthrene-like heterocycles through organocatalytic ANRORC reaction. The method allows for the generation of compounds with bright fluorescence exhibiting potential applications in various solvents. The reaction conditions are mild and suitable for a wide range of reactants.
Article
Chemistry, Organic
Roman A. Irgashev, Alexander S. Steparuk, Gennady L. Rusinov
Summary: A series of compounds containing thieno[3,2-b]indole and coumarin parts were synthesized using a one-pot procedure. The synthesis was achieved by reacting 3-aminothieno[3,2-c]coumarins, generated in situ from 3-aminothieno[3,2-c]coumarin-2-carboxylates, with arylhyrazines. Additionally, the target compounds were successfully synthesized from available 4-hydroxycoumarins.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Organic
Mahmood Kamali
Summary: A new green method has been presented for the synthesis of novel derivatives pyrano[4,3-b]chromenes and chromeno[4,3-b]chromenes, which involves a one-pot three components condensation reaction using SnCl2.2H(2)O as a catalyst in ethanol at 60 degrees C. The syntheses offer operational simplicity, mild reaction conditions, environmentally friendly and easy workup.
SYNTHETIC COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Jinjiao Dong, Xinyue Zhu, Siran Feng, Chaochao Zhang, Zhenming Liu, Xiaoqiang Qiao, Yali Song
Summary: Sixteen 7-phenyl-6H,7H-1,3,4-thiadiazolo[3,2-a]-thiochromeno[4,3-d]pyrimidine compounds containing a fused-ring were designed and synthesized based on the principles of active substructure splicing and bioisosterism. These compounds showed good antifungal activity in vitro against superficial fungi, with compound 5d being particularly sensitive to Trichophyton rubrum. Additionally, they exhibited significant inhibition activity against five plant pathogens, with compound 5l showing a MIC value of 8 μg/mL against Aspergillusniger and Phytophthora infestans.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Zahra Jalili, Reza Tayebee, Farrokhzad M. Zonoz
Summary: A new heterogeneous photoredox nanocatalyst was prepared and characterized, demonstrating high photocatalytic efficiency in the synthesis of chromeno[4,3-b]chromenes. The condensation reaction of aromatic aldehydes, dimedone, and coumarin under green LED light in solventless conditions led to excellent yield, easy work-up, and the ability to recover the catalyst multiple times with minimal activity decrease. The reaction mechanism was shown to involve reactive species such as O-2(-), OH, and h(+), with good stability and reproducibility over at least four runs.
Article
Chemistry, Multidisciplinary
Mahbube Jarrahi, Reza Tayebee, Behrooz Maleki, Alireza Salimi
Summary: Histaminium tetrachlorozincate nanoparticles were successfully prepared and applied as an effective and recoverable photocatalyst for the green and multi-component synthesis of chromenes. The catalyst showed good reusability and the generation of active species during the photocatalytic reaction. Additionally, the stability and ease of separation of the photocatalyst were confirmed, along with other advantages such as cost effectiveness and broad substrate scope.
Article
Chemistry, Organic
Sonam Rai, Abha Bishnoi, Poornima Devi, Nishat Afza
Summary: This study provides a comprehensive description of the molecular vibrations and electronic features of a compound using computer simulation technique. The structure of the compound was confirmed through experimental methods. Quantum chemical calculations were performed to obtain important property parameters and analysis results.
LETTERS IN ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Kabita Baruah, Sangeeta Kalita, Niharika Kashyap, Debanga Bhusan Bora, Subham Paul, Ruli Borah
Summary: A new type of pyranocoumarin derivatives, 7-alkyl or aryl-6H,7H-benzo[f]chromeno[4,3-b]chromen-6-ones (2a-h), was synthesized via a three-component reaction using 25 mol% of N,N-disulfopiperidinium bisulfate [DSPP][HSO4] as a homogeneous recyclable Bronsted acidic ionic liquid catalyst in EtOAc under reflux conditions. The reaction yielded excellent yields (89-97%) of the products within 2-4 hours.
MOLECULAR DIVERSITY
(2023)
Article
Chemistry, Physical
Yuri G. Kappenberg, Pablo A. Nogara, Felipe S. Stefanello, Luis H. Moretto, Patricia M. Santos, Joao B. T. Rocha, Nilo Zanatta, Marcos A. P. Martins, Helio G. Bonacorso
Summary: A new series of tacrine hybrids were designed, synthesized, and evaluated for cholinesterase inhibitory activity. The results showed that three compounds exhibited promising inhibitory potency against BChE.
JOURNAL OF MOLECULAR STRUCTURE
(2022)
Article
Chemistry, Multidisciplinary
Masoumeh Beiranvand, Davood Habibi, Hosein Khodakarami
Summary: A new two-fold interpenetrated pillar-layered metal-organic framework (MOF) was synthesized using zirconium cations, an amine-functionalized ligand, and a linear exo-bidentate bis-pyridine ligand. The structure of the framework was evaluated through various techniques, and its catalytic application was explored for the synthesis of novel 6H-chromeno[4,3-b]quinolin-6-ones. The pure products were obtained with high atom efficiency and characterized using FTIR, NMR, and mass spectrometry techniques.
Article
Chemistry, Multidisciplinary
Xuehua Li
Summary: In this study, a novel heterogeneous nanocatalyst, aluminium nitride, was synthesized and used for the synthesis of chromeno[4, 3-b]chromenes. The potential of aluminium nitride nanocage for delivering the antidiabetic drug, flutamide, was also investigated. The results showed the strongest interaction between flutamide and aluminium nitride.
Article
Chemistry, Multidisciplinary
Abdolali Alizadeh, Azar Rostampoor
Summary: In this research, a simple and chemoselective synthesis of highly fluorescent polysubstituted dihydro-6H-chromeno[4,3-d]pyrazolo[1,5-a]pyrimidin-6-ones containing one chiral stereocenter is presented. The desired products were obtained with short reaction times, easy purification, and medium to high yields under relatively mild reaction conditions.
Article
Biochemistry & Molecular Biology
Ramakant A. Kardile, Aniket P. Sarkate, Avinash S. Borude, Rajendra S. Mane, Deepak K. Lokwani, Shailee Tiwari, Rajaram Azad, Prasad V. L. S. Burra, Shankar R. Thopate
Summary: A novel class of non-camptothecin derivatives, 7,12-dihydrodibenzo[b,h][1,6] naphthyridine and 7H-Chromeno[3,2-c] quinoline, were designed, synthesized, and evaluated for anti-cancer activity. Compounds 8 and 12 demonstrated promising cytotoxicity against A549 and MCF-7 cancer cell lines, suggesting their potential as anti-cancer molecules. Topo I inhibitory activity of 8 and 12 further supported their potential for cancer drug development. In silico ADME prediction studies also showed promising drug-like properties for all derivatives.
BIOORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Zhong-Wei Zhang, Yue-Ying Liu, Si-Yu Wang, Cong-Hai Zhang, Jun Lin
Summary: This study reports an efficient and environmentally friendly method for the synthesis of multisubstituted 7-oxo-7H-chromeno[3,2-c]quinolin-5-ium salts using ambient air as the sole oxidant. The salts were prepared through metal-free cascade intermolecular cycloaddition/oxidation reaction. The resulting salts can be further transformed to diverse synthetically useful compounds.
Article
Chemistry, Organic
Dong Tang, Yangxiu Mu, Zafar Iqbal, Lili He, Rui Jiang, Jing Hou, Zhixiang Yang, Minghua Yang
Summary: An efficient protocol has been developed for the synthesis of pyrazolo[4,3-c]quinoline derivatives using (1H-pyrazol-5-yl)anilines and readily available alcohols/amines. The strategy successfully converted a wide range of substrates with diverse functional groups to the corresponding products in moderate to good yields under optimal reaction conditions, and also showed compatibility with thiol and amino acid for accessing pyrazolo[4,3-c]quinoline derivatives.
JOURNAL OF HETEROCYCLIC CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Deblina Roy, Gautam Panda
Article
Chemistry, Organic
Amit Kumar, Gautam Panda
Summary: In this study, a novel reaction method utilizing Magnesium chloride (MgCl2) catalysis was successfully developed for the highly C3-selective ring-opening reaction of 2,3-epoxy alcohols with N-nucleophiles and sodium azide. The reaction proceeded under mild conditions and showed high yields of the desired 3-amino-1,2 diols and 3-azido-1,2 diols, demonstrating practicality and broad functional group tolerance.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Physical
Deblina Roy, Kasim Ali, Gautam Panda
Summary: The study reveals a method using Wilkinson catalyst for hydroacylation simplifies the synthesis of bedaquiline analogs with reduction of steps. Direct installation of three crucial aryl rings in the reaction leads to a series of bedaquiline analogs.
JOURNAL OF MOLECULAR STRUCTURE
(2021)
Article
Chemistry, Multidisciplinary
Deblina Roy, Grace Kaul, Abdul Akhir, Ashok Kumar Sharma, Satyen Saha, Sidharth Chopra, Gautam Panda
Summary: A library of diarylmethyl amines targeting ESKAPE bacterial pathogens was synthesized, and compounds with potent antibacterial activity against Gram-positive bacteria were identified. The presence of lipophilic and nitrogenous components was found to be important for antibacterial activity.
Article
Chemistry, Organic
Amit Kumar, Gaurav Sharma, Sanjeev K. Shukla, Gautam Panda
Summary: A tandem reaction involving semipinacol rearrangement and aldehyde arylation or alkylation has been discovered. This reaction allows for the formation of functionalized 1,3-diols bearing three consecutive tertiary stereocenters from various trisubstituted 2,3-epoxy alcohols and Grignard reagents. The resulting 1,3-diols are confirmed to exist in the anti configuration.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Medicinal
Amit Kumar, Neetu Kumari, Sandeep Bhattacherjee, Umamageswaran Venugopal, Shahid Parwez, Mohammad Imran Siddiqi, Manju Y. Krishnan, Gautam Panda
Summary: Novel chemical compounds were discovered to inhibit the bc1 complex mutant of Mycobacterium tuberculosis, with two molecules showing MICs of 8 and 16 mu M, compared to MICs of 128 and 256 mu M against the wild type. These compounds were bactericidal to wild type bacteria under hypoxic conditions at concentrations much lower than their MICs, and showed synergy with an inhibitor of the bc1 complex in inhibiting bacterial growth.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Kasim Ali, Gautam Panda
Summary: An efficient transition-metal-free multicomponent approach to the regioselective synthesis of highly substituted N-alkylpyrazoles through 1,6-addition of pyrazole (in situ generated from alpha,beta-unsaturated aldehyde and hydrazide) to para-Quinone Methides has been developed. The N-alkylpyrazole containing triarylmethanes having several heteroaryl rings (quinoline, pyridine, thiophene) at the central methine carbon atom was developed. This chemical process may be used for large-scale synthesis and provides a novel way to produce triarylmethanes with diverse functional groups.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Review
Chemistry, Medicinal
Indranil Chatterjee, Kasim Ali, Gautam Panda
Summary: This review critically analyzes the synthetic strategies and anticancer activities of benzoxazines and benzoxazepines compounds reported from 2010 onwards. The structure-activity relationship of the benzoxazine and benzoxazepine scaffolds containing bioactive compounds is also studied, focusing on how structural modification affects their anticancer activity.
Review
Chemistry, Multidisciplinary
Arpita Banerjee, Indranil Chatterjee, Gautam Panda
Summary: This article discusses the significance of tyrosine as a chiral pool in the synthesis of alkaloids, and compares synthetic steps, overall yield, and other factors between tyrosine-based and non-tyrosine-based routes.
Article
Chemistry, Multidisciplinary
Saroj Maji, Souvik Barman, Gautam Panda
Summary: In this study, a novel synthetic route towards nintedanib was developed using a stereoselective intramolecular cyclization strategy to convert beta-keto amide into a 3-acyloxindole derivative, an important scaffold for nintedanib synthesis. The condensation of the oxindole scaffold with a synthesized amine derivative led to the successful synthesis of nintedanib.
Article
Chemistry, Organic
Indranil Chatterjee, Gautam Panda
Summary: This paper describes a palladium-catalyzed regioselective reaction of propargylic carbonate with thiophenols and benzene selenol. The addition of thiols to propargylic carbonates provides an atom-economic and effective process. The reaction proceeds through hydrothiolation to produce mono(arylthiol) alkenes and hydrothiolation followed by Tsuji-Trost type substitution to form bis(arylthiol) alkenes by controlling the equivalence of thiophenols. This coupling reaction exhibits good tolerance towards functional groups and leads to the formation of highly functionalized alkenylation products via the formation of new C-S and C-Se bonds.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Kasim Ali, Indranil Chatterjee, Gautam Panda
Summary: A simple and efficient metal-free approach was developed for synthesizing 4-thio-substituted chroman and diarylmethyl thioethers, providing good yields and tolerance for labile functional groups. This method is applicable to large-scale synthesis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Kasim Ali, Gurudayal Prajapati, Ravi Sankar Ampapathi, Gautam Panda
Summary: The reductive coupling between allylic sulfonylhydrazones and aryl boronic acids can efficiently generate 1,3-diarylpropene systems under mild reaction conditions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Arpita Banerjee, Gautam Panda
Summary: In this study, a base mediated, transition metal-free intermolecular epoxide ring opening reaction followed by intramolecular aromatic nucleophilic substitution (SNAr) was developed to synthesize separable diastereomers of selected benzo[b][1,4,5]oxathiazepine 1-oxides. This strategy allows the formation of both C-N and C-O bonds simultaneously in a single step. The method has a wide substrate scope, uses simple reaction conditions, and is applicable for synthesizing bioactive molecules with similar skeletons as benzoxathiazepine 1-oxides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Kasim Ali, Prajjval Mishra, Awnish Kumar, Damodara N. Reddy, Sushobhan Chowdhury, Gautam Panda
Summary: In this article, the synthesis, structure-reactivity relationships, and synthetic applications of quinone methides are discussed. The formation of intermediates during bioactivation and potential chemical manifestations leading to toxicity in biological systems are also covered.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
