{"title":"One pot synthetic approach to 2-methyl-5-phenyl-7-amino-[1,3,4]-thiadiazolo[3,2-a]pyrimidine-6-carbonitrile derivatives with antifungal evaluation","authors":"Rimpi Saikia, Jumi Bharali, Sukanya Borthakur, Pabitra Kumar Kalita, Pradyut Sarma, Prakash Jyoti Saikia, Mintu Maan Dutta, Susanta Kumar Borthakur","doi":"10.1002/jhet.4801","DOIUrl":"10.1002/jhet.4801","url":null,"abstract":"<p>Novel 2-methyl-5-phenyl-7-amino-[1,3,4]-thiadiazolo[3,2-<i>a</i>]pyrimidine-6-carbonitrile derivatives <b>3</b> were synthesized from 2-amino-5-methyl-1,3,4-thiadiazole <b>1</b> and benzylidinemalononitrile <b>2</b> in ethanol by refluxing the mixture with catalytic amount of NaOH. The structures of all compounds were characterized by elemental analysis, IR, MS, and <sup>1</sup>H nuclear magnetic resonance spectra. The newly synthesized compounds were also seen as an affective fungicide against <i>Rhizoctonia solani</i> and <i>Trichoderma</i> sp., two fungal microbes causing diseases in rice plants.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 5","pages":"771-777"},"PeriodicalIF":2.4,"publicationDate":"2024-03-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140117489","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Synthesis of a novel fused thieno-pyrimidine with tetrazole analogs","authors":"Muthirevula Rajeswari, Begari Nagaraju, Venkata Rao Chunduri, Bhekumuzi Gumbi, Suresh Maddila","doi":"10.1002/jhet.4798","DOIUrl":"10.1002/jhet.4798","url":null,"abstract":"<p>This current investigation represents the new series of fused thieno-pyrimidine with synthesized tetrazole analogs (6a–j). Intermediates thieno-[2,3-d]-pyrimidine were prepared by utilizing the Gewald method, and tetrazole (5a–j) was synthesized by [3 + 2] cycloaddition of azide and appropriate nitrile. All the prepared novel molecules were characterized and confirmed by <sup>1</sup>HNMR, <sup>13</sup>CNMR, LC-MS, and FT-IR spectral analysis.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 5","pages":"778-782"},"PeriodicalIF":2.4,"publicationDate":"2024-03-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140125926","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Ionic liquid-supported copper-catalyzed synthesis of 2H-indazoles under microwave irradiation","authors":"Upala Dasmahapatra, Kaushik Chanda, Barnali Maiti","doi":"10.1002/jhet.4800","DOIUrl":"10.1002/jhet.4800","url":null,"abstract":"<p>Five-membered indazoles are recognized as a special scaffold having a broad spectrum of pharmacological properties among other heterocyclic compounds. New methods must be developed for the effective synthesis of 2<i>H</i>-indazole because of the exceptionally high biological activity of compounds containing a 2<i>H</i>-indazole core. We present the ionic liquid-supported copper-catalyzed one-pot synthesis of 2<i>H</i>-indazoles under microwave irradiation, continuing our ongoing investigation of the potential uses of bioactive compounds produced in the lab. The use of microwave and ionic liquid-supported catalyst makes this process greener and more highly energy efficient than the conventional reported methods. Overall, by forming consecutive C-N and N-N bonds with the help of an ionic liquid-supported copper catalyst, we have developed a novel green one-pot technique for the synthesis of the 2<i>H</i>-indazole motifs in very high yield.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 5","pages":"761-770"},"PeriodicalIF":2.4,"publicationDate":"2024-03-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140106626","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Gordana Tasic, Nikola Mitrovic, Milena Simic, Mladen Koravovic, Predrag Jovanovic, Milos Petkovic, Milos Jovanovic, Branka Ivkovic, Vladimir Savic
{"title":"Synthesis of hydantoins from N-Boc protected amino acid derived amides using polymer-supported PPh3/CBr4 as a reagent","authors":"Gordana Tasic, Nikola Mitrovic, Milena Simic, Mladen Koravovic, Predrag Jovanovic, Milos Petkovic, Milos Jovanovic, Branka Ivkovic, Vladimir Savic","doi":"10.1002/jhet.4802","DOIUrl":"10.1002/jhet.4802","url":null,"abstract":"<p>Hydantoin derivatives are versatile structural motifs found in natural products and various compounds with different biological or other properties. Due to their importance in both organic and medicinal chemistry, a number of synthetic procedures have been developed. In this article, a novel methodology utilizing <i>N</i>-Boc protected amino acid amides for their preparation has been described. The cyclisation process was accomplished using solid supported PPh<sub>3</sub> and CBr<sub>4</sub> as reagents affording substituted hydantoins in moderate to good yields (40%–77%).</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 5","pages":"753-760"},"PeriodicalIF":2.4,"publicationDate":"2024-03-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140070043","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Alexander A. Larin, Ekaterina V. Dubasova, Ivan V. Ananyev, Konstantin A. Monogarov, Galina A. Gazieva, Leonid L. Fershtat
{"title":"New energetic 1,2,4-triazole-nitrofuroxan hybrids","authors":"Alexander A. Larin, Ekaterina V. Dubasova, Ivan V. Ananyev, Konstantin A. Monogarov, Galina A. Gazieva, Leonid L. Fershtat","doi":"10.1002/jhet.4797","DOIUrl":"10.1002/jhet.4797","url":null,"abstract":"<p>New promising energetic materials comprised of 1,2,4-triazole and furoxan rings and bearing explosophoric nitro group were rationally designed and synthesized. All newly prepared compounds were thoroughly characterized and their physicochemical properties were estimated. In the newly synthesized series, (1,2,4-triazolyl)furoxan <b>4</b> is completely insensitive to impact and friction and possesses good detonation performance (D = 8.4 km s<sup>−1</sup>; P = 33 GPa) enabling its further exploration as a promising high-energy material.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 5","pages":"713-722"},"PeriodicalIF":2.4,"publicationDate":"2024-03-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140055479","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Gurinder Kaur, Rajiv Sharma, Ashu, Geetakshi Arora, Atamjit Singh, Preet Mohinder Singh Bedi, Kundan Singh Bora
{"title":"Recent developments in synthetic strategies and pharmacological outcomes of synthetic xanthine oxidase inhibitors: A comprehensive review","authors":"Gurinder Kaur, Rajiv Sharma, Ashu, Geetakshi Arora, Atamjit Singh, Preet Mohinder Singh Bedi, Kundan Singh Bora","doi":"10.1002/jhet.4796","DOIUrl":"10.1002/jhet.4796","url":null,"abstract":"<p>Xanthine oxidase is an important enzyme in purine metabolism that converts hypoxanthine to xanthine and subsequently xanthine to uric acid. Its elevated levels result in an abnormal accumulation of uric acid that results in gout and other pathological conditions, which makes it a prime target for the management of gout. Considering this, numerous reports have been published by the various research groups across the globe focusing on the development of effective xanthine oxidase inhibitors. On that ground, numerous review articles are also available describing the pharmacological outputs of these reports, but a composition highlighting the synthetic strategies used in these research works is still missing. This review will focus on various synthetic strategies adopted by different research groups in developing xanthine oxidase inhibitors with their pharmacological outcomes, along with structure activity relationships. This review will help researchers and pharmaceutical chemists in the design and development of new xanthine oxidase inhibitor leads that are highly efficient and have fewer side effects than existing ones.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 5","pages":"723-752"},"PeriodicalIF":2.4,"publicationDate":"2024-03-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140055443","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Adriano F. Camargo, Genilson S. Pereira, Mateus Mittersteiner, Mário A. Marangoni, Paulo A. Moraes, Helio G. Bonacorso, Marcos A. P. Martins, Nilo Zanatta
{"title":"Regioselective synthesis of (Z)-5-methylene-containing morpholin-2-ones","authors":"Adriano F. Camargo, Genilson S. Pereira, Mateus Mittersteiner, Mário A. Marangoni, Paulo A. Moraes, Helio G. Bonacorso, Marcos A. P. Martins, Nilo Zanatta","doi":"10.1002/jhet.4795","DOIUrl":"10.1002/jhet.4795","url":null,"abstract":"<p>An efficient, one-pot, protecting-group-free, and regioselective protocol to obtain enantiomerically pure (<i>Z</i>)-5-methylene-containing morpholin-2-ones, using α-amino acids and 5-bromo-4-methoxy enones as selective starting materials, is reported. The reaction was fully selective in providing the (<i>Z</i>)-regioisomer in all cases, regardless of the α-amino acid used; however, when a secondary amino group was used, only the (<i>E</i>)-isomer was observed. The synthesized compounds were obtained at yields of up to 92%, and their structure was unambiguously assigned by x-ray and 2D-NMR experiments.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 5","pages":"703-712"},"PeriodicalIF":2.4,"publicationDate":"2024-02-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139981594","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Guofang Jiang, Can Zhang, Xiaohong Xing, Jinbo Ouyang, Hong Yang, Zongbo Xie, Zhanggao Le
{"title":"Synthesis of 1-(4-hydroxybutyl)-2-benzoyl indoles from 2-pyrrolidine benzaldehydes and α-bromoacetophenones in deep eutectic solvent","authors":"Guofang Jiang, Can Zhang, Xiaohong Xing, Jinbo Ouyang, Hong Yang, Zongbo Xie, Zhanggao Le","doi":"10.1002/jhet.4790","DOIUrl":"10.1002/jhet.4790","url":null,"abstract":"<p>A novel and highly efficient method for the synthesis of 1-(4-hydroxybutyl)-2-benzoyl indoles from 2-pyrrolidine benzaldehyde and <i>α</i>-bromoacetophenone in a choline chloride (ChCl)/ZnCl<sub>2</sub> eutectic mixture was developed. This method, which does not require any catalyst, additive, or alkali, is useful for realizing tandem cyclization reactions. Several indoles were produced after cyclization and ring opening processes. Not all the compounds obtained are reported in the literature. This synthetic strategy proves that deep eutectic solvents can replace catalysts and organic solvents. Consequently, this is an environmentally friendly strategy that has significant potential in the development of green and sustainable chemistry.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 5","pages":"685-692"},"PeriodicalIF":2.4,"publicationDate":"2024-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139946194","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Synthesis of benzo[b]pyran, 3,4 dihydropyrano[c]chromene and their new furan derivatives using Cu(II) complex of tetradentate Schiff-base supported on silica as a nanocatalyst","authors":"Hashem Sharghi, Elahe Mashhadi, Seyyede Faeze Razavi, Mahdi Aberi","doi":"10.1002/jhet.4794","DOIUrl":"10.1002/jhet.4794","url":null,"abstract":"<p>Cu(II) Complex of tetradentate Schiff-base supported on silica [Cu(II) Schiff-base@-SiO<sub>2</sub>] catalyzed reactions of aryl aldehydes with carbonyl compounds (dimedon/4-hydroxy coumarin/1,3-cyclohexadion) and malononitrile in aqueous media (H<sub>2</sub>O:EtOH) to preparation of benzo[<i>b</i>]pyrans and 3,4-dihydropyrano[<i>c</i>]chromanes. Also, using this nanocatalyst, 2-(5-substituted phenyl)furan-2-carboxaldehyde derivatives with carbonyl compounds (dimedon/4-hydroxy coumarin/1,3-cyclohexadion) and malononitrile gave novel tetrahydrobenzo[<i>b</i>]pyran and 3,4-dihydropyrano[<i>c</i>]chromane derivatives in high yields in H<sub>2</sub>O:EtOH under reflux conditions. The key advantages of this catalytic systems are the formation of novel products, high yields (78%–93%), short reaction time, broad substrate scope, environmentally friendly reaction conditions and also, without need to column chromatography for purification. Furthermore, the nanocatalyst can be reused six times without losing catalytic activity.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 5","pages":"693-702"},"PeriodicalIF":2.4,"publicationDate":"2024-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139946227","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Subramani Selvi, Arun Kannan, John M. Jayaraj, Thangavel Selvi, Muthusamy Karthikeyan, Chidambaram Prahalathan, Natarajan Sampath, Kannupal Srinivasan
{"title":"Synthesis and biological evaluation of 3-hydroxypyrazoles as aquaporin 9 inhibitors","authors":"Subramani Selvi, Arun Kannan, John M. Jayaraj, Thangavel Selvi, Muthusamy Karthikeyan, Chidambaram Prahalathan, Natarajan Sampath, Kannupal Srinivasan","doi":"10.1002/jhet.4793","DOIUrl":"10.1002/jhet.4793","url":null,"abstract":"<p>A series of 3-hydroxypyrazole derivatives have been synthesized by a base-promoted reaction of nitro-substituted donor–acceptor cyclopropanes with hydrazines. The synthesized compounds have been investigated for their ability to inhibit aquaporin 9 (AQP9) in rat Leydig cells (LC-540). The protein data bank structure for AQP9 was predicted using homology modeling; and the protein–ligand interaction for the synthesized hydroxyl pyrazole derivatives were analyzed using molecular modeling and docking studies. The results of in silico analyses showed that compound <b>5b</b> had a higher binding affinity with AQP9 than other compounds. Further, in vitro studies conducted in LC-540 cells confirmed that compound <b>5b</b> effectively inhibits AQP9. Hence, compound <b>5b</b> may be used as an inhibitor in enhancing our understanding of AQP9 function, and in the treatment of several diseases.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 4","pages":"669-679"},"PeriodicalIF":2.4,"publicationDate":"2024-02-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139835158","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}