Article
Biochemistry & Molecular Biology
Cesia M. Aguilar-Morales, Jorge Gustavo Araujo-Huitrado, Yamile Lopez-Hernandez, Claudia Contreras-Celedon, Alejandro Islas-Jacome, Angelica Judith Granados-Lopez, Cesar R. Solorio-Alvarado, Jesus Adrian Lopez, Luis Chacon-Garcia, Carlos J. Cortes-Garcia
Summary: This study presents a high-order multicomponent reaction to obtain novel linked 1,5-disubstituted tetrazole-1,2,3-triazole hybrids in low to moderate yield. The cascade process involves Ugi-azide, bimolecular nucleophilic substitution (S(N)2), and copper-catalyzed alkyne-azide reaction (CuAAC), forming six new bonds. The synthesized hybrid compounds show potential as drug candidates for breast cancer treatment, especially those with cyclohexane and halogens in their structures, although further assays are needed to fully understand their effects on cancer cell hallmarks.
Article
Chemistry, Multidisciplinary
Saad Shaaban, Amira Zarrouk, Dominique Vervandier-Fasseur, Yasair S. Al-Faiyz, Hany El-Sawy, Ismail Althagafi, Pierre Andreoletti, Mustapha Cherkaoui-Malki
Summary: Organoselenium compounds were synthesized via Ugi and Ugi-azide reactions, with tetrazole and pseudopeptide-based compounds showing antioxidant properties, while quinone and pseudopeptide-based compounds exhibited prooxidant activities. Additionally, tetrazole-based and selenopeptide compounds demonstrated good GPx-like activity, suggesting potential as drug candidates for myelin diseases.
ARABIAN JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Organic
Jun Xiong, Hui-Ting He, He-Yu Yang, Zhi-Gang Zeng, Cheng-Ran Zhong, Hang Shi, Meng-Ling Ouyang, Yuan-Yuan Tao, Yong-Long Pang, Yang-Hong Zhang, Bo Hu, Zi-Xiang Fu, Xiao-Lei Miao, Hai-Li Zhu, Gang Yao
Summary: A new one-pot preparation method for 4-tetrazolyl-3,4-dihydroquinazolines is reported in this study, which involves Ugi-azide reactions of 2-azidobenzaldehydes, amines, trimethylsilyl azide, and isocyanides. The obtained azide intermediates were sequentially subjected to a Palladium-catalyzed azide-isocyanide cross-coupling/cyclization reaction to yield 4-tetrazolyl-3,4-dihydroquinazoline derivatives. Compound 6c exhibited significant inhibition against breast cancer cells and showed broad applications in synthesis and medicinal chemistry.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Materials Science, Multidisciplinary
Meryem S. S. Akdemir, Birgit Huber, Marina Simian, Hatice Mutlu, Patrick Theato
Summary: The unique molecular structure of tetrazoles, consisting of a five-membered ring with four nitrogen atoms, has great potential in polymer chemistry. While research on tetrazole-containing polymers with pendant chains has been extensively studied, the synthesis of main chain tetrazole-based polymers has not been widely explored. This study demonstrates the possibility of polymer formation using the Ugi-azide-four-multicomponent polymerization strategy for main chain 1,5-disubstituted-1H-tetrazole-based compounds. The synthesized polymers displayed interesting properties such as adjustable glass-transition temperature and thermal stability.
ACS APPLIED POLYMER MATERIALS
(2023)
Article
Chemistry, Applied
Teppei Abe, Kazuki Kobayashi, Seiya Kikukawa, Yuuki Kanai, Takeshi Hata
Summary: This study investigated the reaction of 1-azido-2-(2,2-dihalovinyl)arenes with Rh2(esp)2 catalyst, successfully synthesizing 2,3-dihaloindoles and 2-haloquinoxaline. In the reaction of the 2-chloro-2-iodovinyl group, the iodo group selectively rearranged to yield 2-chloro-3-iodoindoles.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Gangam Srikanth Kumar, Stefano Racioppi, Eva Zurek, Qing Lin
Summary: This article reports the design of a super fast bioorthogonal ligation reactant pair, enabling rapid bioorthogonal labeling on live cells.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Engineering, Environmental
Yaqun Dong, Yuji Liu, Wei Huang, Yongxing Tang
Summary: In this study, two isomeric compounds were synthesized using a new method, and their energetic properties were examined. The results showed that one of the compounds exhibited better detonation performance, higher thermal stability, and lower mechanical sensitivities, suggesting its potential as an energetic material.
CHEMICAL ENGINEERING JOURNAL
(2022)
Article
Chemistry, Organic
Israel Nino-Pantoja, Arturo Gallardo-Alfonzo, Melchor Solis-Santos, Mario Ordonez, Claudia Contreras-Celedon, Alejandro Islas-Jacome, Luis Chacon-Garcia, Carlos J. Cortes-Garcia
Summary: A novel bis-heterocyclic system containing 1,2-dihydro-3H-pyrrolo[3,4-b]indolizin-3-one and 1,5-disubstituted tetrazole moieties was designed and synthesized as a Copper (II) recognizing agent. The compounds were prepared using a novel one-pot synthetic strategy involving four-step reactions. The photophysical properties of the obtained compounds were evaluated for their response to Copper (II).
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Qiang Zheng, Andre Boltjes, Alexander Domling
Summary: A series of tetrazole-linked dibenzo[b,f][1,4]oxazepines are synthesized through a short sequence involving an Ugi tetrazole reaction, S(N)Ar cyclization, and oxidation to afford the target tricyclic heterocyclic scaffold. A 1000-member library of these compounds is generated and the physicochemical properties are analyzed.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Multidisciplinary
Yuangang Xu, Lujia Ding, Dongxue Li, Pengcheng Wang, Qiuhan Lin, Ming Lu
Summary: A series of polynitro-substituted 5,6-dihydrodiimidazo[1,2-a:2',1'-c]pyrazine energetic compounds were synthesized by cyclization and nitration of biimidazole. The structures and properties of the compounds were investigated, and compounds 3-6 were found to be thermally stable and insensitive. They showed potential as replacements for TNT due to their superior detonation performances and good stabilities.
CRYSTAL GROWTH & DESIGN
(2022)
Article
Chemistry, Organic
Sangh Priya Singh, Asheesh Kumar, Ruchir Kant, Ajay Kumar Srivastava
Summary: A convenient method for the synthesis of less explored pyrrolo[1,2-a]pyrazine-3,6(2H,4H)-diones from Ugi adducts is described. The method involves acid-mediated cyclization of Ugi adducts to form dihydropyrazinones followed by gold(I)-catalyzed regioselective annulation. By reacting various substituted dihydropyrazinones under optimized conditions, densely functionalized pyrrolo[1,2-a]pyrazine-3,6(2H,4H)-diones were obtained in good-to-excellent yields. It was also observed that some acetone-derived Ugi adducts produced 7-acyl-pyrroloimidazolones as byproducts during TFA-mediated cyclization.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Mariia B. Litvinchuk, Anton V. Bentya, Alina M. Grozav, Nina D. Yakovychuk, Alina O. Palamar, Lesya M. Saliyeva, Nataliia Yu. Slyvka, Svitlana V. Shishkina, Mykhailo V. Vovk
Summary: A convenient and efficient method for the synthesis of novel 1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-8-carboxylic acids was proposed. The compounds were synthesized through a reaction between (3-oxopiperazine-2-ylidene)ethanoates and 2-bromo-1,1-diethoxyethane, with intermediate methyl 1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-8-carboxylates also being isolated. Another method to transform the carboxylic acids into carboxamides was developed, achieving yields of 31-78%. The synthesized compounds displayed moderate antimicrobial and antifungal activity, with some of the carboxamides showing antioxidant effects comparable to ascorbic acid.
MONATSHEFTE FUR CHEMIE
(2023)
Article
Chemistry, Organic
Chakrapani Sanaboina, Samir Kumar Mandal, Samaresh Jana
Summary: A simple and efficient synthesis method for pyrrolo[1,2-a]pyrazine has been developed using Schiff base formation, intramolecular cyclization (or N-alkylation), and Pictet-Spengler type reaction (hetero-aromatisation). This metal-free approach is cost-effective and time-saving, allowing the synthesis of complex nitrogenous scaffolds from simple starting materials.
LETTERS IN ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Mingjun Xiao, Yi-Kang Zhang, Ranran Li, Shengtao Li, Di Wang, Peng An
Summary: Aryl azide-tetrazole probes can be activated by click reaction and light, leading to high signal-to-noise ratio and spatiotemporal resolution.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Sultan Pathan, Girdhar Pal Singh
Summary: A new series of tetrazole tetrahydrobenzo[b]thiophene compounds were synthesized through Gewald synthesis followed by Ugi multicomponent reaction, with compound 10k showing the most potent in vitro activity and high selectivity compared to miltifosine. The identity of newly synthesized compounds was confirmed through spectroscopic analysis, highlighting the potential of these compounds as antileishmanial agents.
JOURNAL OF SAUDI CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Abuzar Taheri, Douglas R. MacFarlane, Cristina Pozo-Gonzalo, Jennifer M. Pringle
Article
Chemistry, Physical
Abuzar Taheri, Douglas R. MacFarlane, Cristina Pozo-Gonzalo, Jennifer M. Pringle
SUSTAINABLE ENERGY & FUELS
(2018)
Article
Chemistry, Organic
Mehdi Ghandi, Abuzar Taheri, Alireza Abbasi
JOURNAL OF HETEROCYCLIC CHEMISTRY
(2010)
Article
Biochemistry & Molecular Biology
Mehdi Ghandi, Abuzar Taheri
Article
Chemistry, Organic
Mehdi Ghandi, Nahid Zarezadeh, Abuzar Taheri
Article
Chemistry, Organic
Mehdi Ghandi, Abuzar Taheri, Alireza Abbasi
Article
Chemistry, Organic
Mehdi Ghandi, Abuzar Taheri, Abolfazl Hasani Bozcheloei, Alireza Abbasi, Reza Kia
Article
Chemistry, Organic
Mehdi Ghandi, Seyed Jamal Tabatabaei Rezaei, Ahmad Yari, Abuzar Taheri
TETRAHEDRON LETTERS
(2008)
Article
Chemistry, Organic
Mehdi Ghandi, Ahmad Yari, Seyed Jamal Tabatabaei Rezaei, Abuzar Taheri
TETRAHEDRON LETTERS
(2009)
Article
Chemistry, Organic
Mehdi Ghandi, Nahid Zarezadeh, Abuzar Taheri
TETRAHEDRON LETTERS
(2011)
Article
Chemistry, Organic
Mehdi Ghandi, Nahid Zarezadeh, Abuzar Taheri
TETRAHEDRON LETTERS
(2012)
Article
Chemistry, Organic
Abuzar Taheri, Ronald J. Quinn, Mikhail Krasavin
TETRAHEDRON LETTERS
(2014)
Article
Chemistry, Multidisciplinary
Mehdi Ghandi, Parham Asgari, Abuzar Taheri, Alireza Abbasi
CENTRAL EUROPEAN JOURNAL OF CHEMISTRY
(2010)