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3. Contributors

Author

Aashruti Agrawal, Rascón-Chu Agustín, Hanan B. Ahmed, Bhavna Alke, Sánchez-Villegas J. Alfonso, Sukumaran Anil, Balaprasad Ankamwar, Geeta Arya, Rajib Bandopadhyay, Raju Biswas, Mengna Cao, Soma Chakraborty, Norma B. D'Accorso, Pandurang A. Dalavi, Anurag Dutta, Hossam E. Emam, Shahira M. Ezzat, Ohlmaier-Delgadillo Federico, Gomez-Rodriguez Gabriel H., Dipak D. Gadade, Nancy Lis Garcia, Qing Gu, Félix-Arias K. Guadalupe, Nidhi Gupta, Surabhi Gupta, Yusuf Haggag, Urmi Halder, Xiuting Hu, Harsha Jain, Supriya Jain, M.V. Jithin, Renjith P. Johnson, Ashutosh Kabiraj, Deepak A. Kulkarni, Mikhail I. Kusayin, Moitri Let, Lara-Espinoza Claudia Lizeth, Jitender Madan, Krishnendu Majhi, Verónica E. Manzano, Shirui Mao, Ming Miao, D.B. Mondal, Sesha Subramanian Murugan, Fangfang Ni, Surendra Nimesh, Purva Pingle, Ashwini Prabhu, Namitha K. Preman, Pradipta Purkayastha, R. Raguavaran, Carlos Rodriguez Ramirez, Vinitha Rani, Anton B. Rasin, Pavan B. Rathi, Evangelina Repetto, Mohamed A. Salem, Jaiprakash N. Sangshetti, Sandesh G. Sanjeeva, Jayanta K. Sarmah, Sanjib Sarmah, D.K. Sharma, Lokesh Sharma, Saurabh Shrivastava, Yujiao Sun, Usman T. Syed, Chandrakant Tagad, Syed N. Taqui, Shareefraza J. Ukkund, Roland Ulber, Rosa V. Usoltseva, Jayachandran Venkatesan, Hujun Xie, Awesh K. Yadav, Narayani Yadav, Ahmed Zayed, and Gomeztagle-Romero M. Zuleth

Published
2022
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6. List of contributors

Author

Ahmed S. Abo Dena, Caleb Acquah, Tanvir Ahmed, Azilah Ajit, Yahya S. Al-Awthan, Tânia Albuquerque, Sukumaran Anil, Nuvia Marina Apolonio–Hernandez, Leonard Ionut Atanase, Omar Bahattab, Anindita Behera, Muhammad Bilal, Branko Bugarski, A.C. Campa-Mada, Ireri Alejandra Carbajal-Valenzuela, E. Carvajal-Millan, Long Chen, Wai Teng Cheng, Custodiana A. Colmenarez Lobo, Diana Costa, Eduardo Costa, Pandurang Appana Dalavi, Michael K. Danquah, Y. De Anda-Flores, Harshal Deshmukh, Amal Kumar Dhara, Ibrahim M. El-Sherbiny, Rúben Faria, Ana Angelica Feregrino-Pérez, M.D. Figueroa-Pizano, D.A.S. Gamage, Beatriz González-Arias, Natanamurugaraj Govindan, Ramón Gerardo Guevara-González, Diana Vanesa Gutierrez-Chavez, Md Saquib Hasnain, Shafiul Hossain, Muhammad Imran, Hafiz M.N. Iqbal, Jaison Jeevanandam, Alejandra Jimenez-Hernandez, Zhengyu Jin, Sumaya F. Kabir, Krishnan Kanny, Jaya Lakkakula, J. Lizardi-Mendoza, Manuela Machado, T. Madhujith, Gaanty Pragas Maniam, Verónica E. Manzano, A.L. Martínez-López, K.G. Martínez-Robinson, David Julian McClements, Ming Miao, Milan Milivojevic, Md. Minhajul Islam, Aurelie Sarah Mok Tsze Chung, Mohammad S. Mubarak, Naveed Muhammad, Hira Munir, Sesha Subramanian Murugan, Amit Kumar Nayak, Ana R. Neves, Ahmed Olatunde, Ivana Pajic-Lijakovic, Dilipkumar Pal, Aristeidis Papagiannopoulos, Manuela Pintado, Marcel Popa, Sarmad Ahmad Qamar, Telma Quintela, Stefania Racovita, Hamza Rafeeq, Mohd Hasbi Ab. Rahim, Ashiqur Rahman, Mohammed Mizanur Rahman, Khushboo Raj, Ajay Vasudeo Rane, A. Rascón-Chu, Abdur Rauf, Evangelina Repetto, Enrique Rico-García, Supriyo Saha, Md. Sazedul Islam, Md. Shahruzzaman, Sara Silva, Ângela Sousa, Ahmad Ziad Sulaiman, Sabrina Sultana, Joash Ban Lee Tan, J. Tanori-Cordova, Yong Kiat Teo, Himja Tiwari, Irineo torres-Pacheco, Tabussam Tufail, Silvia Vasiliu, Jayachandran Venkatesan, Eleni Vlassi, Nilesh Shirish Wagh, N.E. Wedamulla, Deepti Yadav, and Zhongyu Yang

Published
2022
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7. Synthesis of Highly Substituted and Enantiomerically Pure 2,3,4-Tris(hydroxyalkyl)pyrrolidines Using a 1,3-Dipolar Cycloaddition Reaction as Key Step

Author

Daniel Vega, Guillermo Alejandro Oliveira Udry, Evangelina Repetto, and Oscar Jose Varela

Subjects
Tris, 010405 organic chemistry, Stereochemistry, Otras Ciencias Químicas, Ciencias Químicas, Azomethine ylide, General Chemistry, 010402 general chemistry, 01 natural sciences, Pyrrolidine, 0104 chemical sciences, chemistry.chemical_compound, chemistry, PYRROLIDINE, 1,3-DIPOLAR-CYCLOADDITION, 1,3-Dipolar cycloaddition, SUGAR ENONE, AZOMETHINE YLIDE, CIENCIAS NATURALES Y EXACTAS, POLYHYDROXYALKYLPYRROLIDINE
Abstract

The major endo cycloadducts with a basic structure of methyl 1-aryl-3-(benzyl or methyl)-6-menthyloxy-7-oxooctahydropyrano[4,3-c]pyrrole-3-carboxylate were subjected to simple chemical transformations (mostly reduction and hydrolysis reactions) to afford pyrrolidine bicyclic systems with varied patterns of substitution and configurations. The cycloadducts have been obtained by the 1,3-dipolar cycloaddition of (S)-2-menthyloxy-2H-pyran-3(6H)-one, derived from D-xylose, with azomethine ylides derived from imines of L-alanine or L-phenylalanine. The synthetic route led to enantiomerically pure 2,3,4-tris(hydroxyalkyl) pyrrolidines possessing a tetrasubstituted carbon stereocenter vicinal to the ring nitrogen atom and carrying a phenyl substituent on the other carbon adjacent to the nitrogen. Fil: Oliveira Udry, Guillermo Alejandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina Fil: Repetto, Evangelina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina Fil: Vega, Daniel Roberto. Comisión Nacional de Energía Atómica. Gerencia del Área Investigaciones y Aplicaciones no Nucleares; Argentina. Comisión Nacional de Energía Atómica; Argentina. Universidad Nacional de San Martín; Argentina Fil: Varela, Oscar Jose. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina

Published
2017
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8. Intramolecular azide-alkene cycloaddition-elimination reaction in an aldohex-2-enonic acid derivative

Author

Oscar Jose Varela, Guillermo Alejandro Oliveira Udry, and Evangelina Repetto

Subjects
Azides, Triazole, Alkenes, 010402 general chemistry, 01 natural sciences, Biochemistry, Medicinal chemistry, Analytical Chemistry, chemistry.chemical_compound, Elimination reaction, Pyrroles, Enzyme Inhibitors, chemistry.chemical_classification, Cycloaddition Reaction, Molecular Structure, 010405 organic chemistry, Alkene, Organic Chemistry, Aromatization, General Medicine, Triazoles, Cycloaddition, 0104 chemical sciences, chemistry, Intramolecular force, 1,3-Dipolar cycloaddition, Azide
Abstract

A 6-azido-2-tosylenolate, obtained from D-glucono-1,5-lactone in six steps, underwent an intramolecular cycloaddition–elimination pathway under mild conditions, yielding a chiral, substituted 5,6-dihydro-4H-pyrrolo[1,2-c]-1,2,3-triazole. The conditions were optimized to give exclusive formation of the triazole. The mechanism appears to involve intramolecular ring closure via a 1,3-dipolar azide–alkene cycloaddition to give a 1,2,3-triazoline, followed by elimination of p-toluenesulfonic acid, leading to aromatization. Triazole products, obtained by chemical modification, are expected to display activity as enzyme inhibitors. Furthermore, partially protected derivatives of the 2-hexenoate were prepared as useful synthetic intermediates.

Published
2019
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9. Synthesis of Enantiomeric Polyhydroxyalkylpyrrolidines from 1,3-Dipolar Cycloadducts. Evaluation as Inhibitors of a β-Galactofuranosidase

Author

Guillermo A. Oliveira Udry, Oscar Varela, Daniel Vega, and Evangelina Repetto

Subjects
Models, Molecular, Ketone, Pyrrolidines, Glycoside Hydrolases, Stereochemistry, Substituent, Molecular Conformation, 010402 general chemistry, 01 natural sciences, Pyrrolidine, 1,3-DIPOLAR CYCLOADDUCTS, purl.org/becyt/ford/1 [https], chemistry.chemical_compound, Hydrolysis, Bridged Bicyclo Compounds, purl.org/becyt/ford/1.4 [https], Enzyme Inhibitors, chemistry.chemical_classification, Bicyclic molecule, Cycloaddition Reaction, 010405 organic chemistry, Otras Ciencias Químicas, Organic Chemistry, Ciencias Químicas, Penicillium, Stereoisomerism, Cycloaddition, 0104 chemical sciences, Amino acid, POLYHYDROXYALKYLPYRROLIDINES, chemistry, Enantiomer, Oxidation-Reduction, CIENCIAS NATURALES Y EXACTAS
Abstract

Enantiomeric 2,3,4-tris(hydroxyalkyl)-5-phenylpyrrolidines have been synthesized from the major cycloadducts obtained by the 1,3-dipolar cycloaddition of sugar enones with azomethine ylides derived from natural amino acids. Reduction of the ketone carbonyl group of the cycloadducts, which possess a basic structure of bicyclic 6-(menthyloxy)hexahydropyrano[4,3-c]pyrrol-7(6H)one, afforded a number of pyrrolidine-based bicyclic systems. A sequence of reactions, which involved hydrolysis of the menthyloxy substituent, reduction, N-protection, and degradative oxidation, afforded varied pyrrolidine structures having diverse configurations and patterns of substitution; in particular, polyhydroxylated derivatives have been obtained. The unprotected products were isolated as pyrrolidinium trifluoroacetates. Because of the furanose-like nature of the target trihydroxyalkyl pyrrolidines, these molecules have been evaluated as inhibitors of the β-galactofuranosidase from Penicillium fellutanum. The compounds showed practically no inhibitory activity for concentration of pyrrolidines in the range of 0.1–1.6 mM. Fil: Oliveira Udry, Guillermo Alejandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina Fil: Repetto, Evangelina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina Fil: Vega, Daniel Roberto. Comisión Nacional de Energía Atómica. Centro Atómico Constituyentes. Gerencia de Investigación y Aplicaciones; Argentina. Universidad Nacional de San Martín. Escuela de Ciencia y Tecnología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina Fil: Varela, Oscar Jose. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina

Published
2016

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