Article
Chemistry, Organic
Koshiro Maegawa, Hiroki Tanimoto, Seiji Onishi, Takenori Tomohiro, Tsumoru Morimoto, Kiyomi Kakiuchi
Summary: Organic azides, particularly alpha-azido secondary acetamides (alpha-AzSAs), have been shown to exhibit unique reactivities with selective conjugation in the presence of other azido moieties. These minimal and unhindered azide structures were found to undergo conjugation prior to other primary alkyl azides in Staudinger-Bertozzi ligation, but were slower than other alkyl azides in propargyl cation-mediated triazole synthesis. The study also demonstrated site-selective integration of functional components onto diazide modular hubs.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Review
Biochemistry & Molecular Biology
Yaqi Zhao, Zhengqi Chai, Qingrui Zeng, Wen-Xiong Zhang
Summary: Nowadays, the click reaction of azides with alkynes has rapidly evolved as an efficient method for synthesizing 1,2,3-triazoles, an important class of N-containing heterocycles. While the 1,4-selective click reaction is well-established, the corresponding 1,5-selective reaction remains less explored, lacking a systematic review. This timely review summarizes the discovery and development of 1,5-selective click reactions of azides with alkynes for synthesizing 1,5-substituted 1,2,3-triazoles, including three types of reactions based on critical reactive intermediates and related mechanistic studies.
Article
Chemistry, Applied
Qiang Tang, Keke Xu, Xinwei He, Yongjia Shang
Summary: A metal-free cascade annulation strategy has been developed for the synthesis of polysubstituted imidazoles and 4-alkenylquinazolines. The reaction proceeds through sequential conjugate addition, annulation/aromatization, and nucleophilic addition/elimination/aromatization steps. The method shows broad substrate scope and high yields, as demonstrated by gram-scale experiments and synthetic transformations.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Applied
Max Roemer, Ian Luck, Nicholas Proschogo
Summary: This paper investigates the synthesis of aryl amines from halobenzenes via copper mediated reactions using sodium azide under mild conditions. The reaction proceeds stepwise through the formation of aryl azides, which are then reduced to amines. The methodology allows for the synthesis of amines from different positions of halobenzenes with electron withdrawing groups. The use of modified stirring bars as heterogeneous catalysts is also demonstrated.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Chao Wang, Qianqian Li, Shilei Wang, Gongming Zhu, Anlian Zhu, Lingjun Li
Summary: A new reaction system was developed for the efficient synthesis of 5-aryl-1,2,3-triazole compounds, featuring low-cost catalyst, clean oxidant, less-toxic additive, and low reaction temperature. This method can provide mild conditions for multi-component synthesis of complex alkynyl or azide donors.
Article
Chemistry, Organic
Michal Kopyt, Michal Tryniszewski, Michal Barbasiewicz, Piotr Kwiatkowski
Summary: Enantioselective Michael addition under high-pressure conditions is an efficient method to synthesize chiral cyclohexanes.
Article
Chemistry, Organic
Xuelun Duan, Nan Zheng, Gongbo Liu, Ming Li, Qiming Wu, Xinhao Sun, Wangze Song
Summary: A novel four-component reaction has been developed for the efficient synthesis of polyfunctionalized triazoles. This reaction involves the formation of four C-N bonds in one step under mild conditions, using alkynes, amines, azides, and 2H-azirines as reactants.
Article
Chemistry, Applied
Valentina Ferraro, Roberto Sole, Marco Bortoluzzi, Valentina Beghetto, Jesus Castro
Summary: The three-coordinated homoleptic Cu(I) complex with 2,6-dimethylphenyl isocyanide in the coordination sphere was easily synthesized and isolated as tetrafluoroborate salt. The complex is highly stable, active and selective toward the copper-catalyzed azide-alkyne cycloaddition, working in neat conditions and in the absence of bases at room temperature. Substrate scope was assessed by testing several different alkynes and azides, resulting in high yields of the corresponding 1,4-disubstituted-1,2,3-triazoles in most cases.
APPLIED ORGANOMETALLIC CHEMISTRY
(2021)
Article
Chemistry, Analytical
Heba A. Aref, Ismail Salama, Shaimaa Mohamed Aboukhatwa, Mohamed A. Helal, Safaa M. Kishk, Mohamed Saleh Elgawish
Summary: A promising click fluorescent probe, 4-azido-7-nitrobenzoxadiazole (NBD-AZ), was introduced for the first time to detect ethinylestradiol (EE) by reacting with its alkyne group. The method produced a highly fluorescent and stable 1,2,3-triazole derivative with the help of copper sulphate and l-ascorbic acid. The suggested approach showed outstanding performance with high sensitivity, selectivity, and a low detection limit.
Article
Chemistry, Organic
Qi Wei, Yan Zhang, Cidan Lv, Changwei Hu, Zhishan Su
Summary: Density functional theory calculations revealed the mechanism and stereoselectivity of chiral guanidine/copper(I) salt-catalyzed stereoselective three-component reaction. The rate-determining step for the noncatalytic cascade reaction was the denitrogenation to generate ketenimine species. Chiral guanidine-amide promoted deprotonation of phenylacetylene and coordinated with copper to activate TsN3 for the Cu(I)-ketenimine species.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Environmental Sciences
Shangying Zhang, Fengna Dai, Zhao Ke, Qi Wang, Chunhai Chen, Guangtao Qian, Youhai Yu
Summary: Porous hollow carboxyl-polysulfone (PH-CPSF) microspheres were synthesized through non-solvent-induced phase separation (NIPS) method, showing high adsorption capacity for cationic dyes. The microspheres exhibit a hollow core structure, high surface area, and strong adsorption ability due to inter-molecular interactions.
Review
Biochemistry & Molecular Biology
AbdElAziz A. Nayl, Ashraf A. Aly, Wael A. A. Arafa, Ismail M. Ahmed, Ahmed I. Abd-Elhamid, Esmail M. El-Fakharany, Mohamed A. Abdelgawad, Hendawy N. Tawfeek, Stefan Brase
Summary: This review focuses on the applications of organic azides in various reactions, including intermolecular and intramolecular reactions under different conditions. The aim is to synthesize basic heterocyclic compounds and their fused analogs. The review categorizes the synthetic methods of organic azides and discusses the functionality of the azido group in chemical reactions. It also covers the synthesis of heterocycles using one-pot domino reactions, the use of catalysts for selective C-H and C-N bond activation, and various other reactions involving organic azides. The review includes recent examples and highlights the mechanistic aspects of the reactions.
Article
Chemistry, Multidisciplinary
Henry Lindner, Willi M. Amberg, Erick M. Carreira
Summary: In this study, unactivated olefins are converted into alkyl azides using bench-stable NaN3 in the presence of FeCl3·6H2O under blue-light irradiation. The reaction exhibits anti-Markovnikov selectivity and can be conducted under mild ambient conditions in the presence of air and moisture.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Ch Venkata Ramana Reddy, G. Ganga Reddy
Summary: A series of new 2-((1-((1-(4-methoxy-3-nitrophenyl)-1H-1,2,3-triazol-4-yl)methyl)1H-indol-3-yl)methylene)malononitrile derivatives were synthesized efficiently via 1,3-dipolar cycloaddition reaction, demonstrating high yields and convenience in operation.
LETTERS IN ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Inorganic & Nuclear
Dominik Moreth, Gerald Hoerner, Victoria V. L. Mueller, Lucia Geyer, Ulrich Schatzschneider
Summary: This study investigates the structure and reactivity of a series of cyclometalated azido complexes through X-ray diffraction analysis and NMR spectroscopy. The reaction rate is found to be positively correlated with the charge density of the metal ion, and the substituents on the alkyne affect the reaction kinetics. Crystal structure analysis reveals different coordination modes of the complexes, unaffected by the substituents on the alkyne. Additionally, the study demonstrates the feasibility of biofunctionalizing metal complexes through the iClick reaction.
INORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Jaswanth S. Bhandaru, Narender Malothu, Raghuram R. Akkinepally
CRYSTAL GROWTH & DESIGN
(2015)
Article
Chemistry, Medicinal
Prabhakar S. Achanta, Rajesh Kumar Gattu, Adavi Rao V. Belvotagi, Raghurarn Rao Akkinepally, Ravi Kumar Bobbala, Appa Rao V. N. Achanta
Letter
Chemistry, Multidisciplinary
Prabhakar S. Achanta, Raghuram Rao Akkinepally, Ravi Kumar Bobbala, Appa Rao V. N. Achanta
MAGNETIC RESONANCE IN CHEMISTRY
(2016)
Article
Biochemistry & Molecular Biology
Meryem Koese, Anke C. Schiedel, Alexander Andreas Bauer, Hermann Poschenrieder, Joachim C. Burbiel, Raghuram Rao Akkinepally, Hans-Dietrich Stachef, Christa E. Mueller
BIOORGANIC & MEDICINAL CHEMISTRY
(2016)
Article
Chemistry, Medicinal
Joachim C. Burbiel, Wadih Ghattas, Petra Kueppers, Meryem Koese, Svenja Lacher, Anna-Maria Herzner, Rajan Subramanian Kombu, Raghuram Rao Akkinepally, Joerg Hockemeyer, Christa E. Mueller
Article
Chemistry, Organic
Triparagiri Ramanivas, Matam Parameshwar, Gaddamanugu Gayatri, Jagadeesh Babu Nanubolu, Ajay Kumar Srivastava
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Medicinal
Balakumar Chandrasekaran, Pran Kishore Deb, Sonja Kachler, Raghuram Rao Akkinepalli, Raghuprasad Mailavaram, Karl-Norbert Klotz
MEDICINAL CHEMISTRY RESEARCH
(2018)
Article
Chemistry, Medicinal
Narender Malothu, Umasankar Kulandaivelu, Malathi Jojula, Shravan Kumar Gunda, Raghuram Rao Akkinepally
CHEMICAL & PHARMACEUTICAL BULLETIN
(2018)
Article
Education, Scientific Disciplines
Srujana Muthadi, Baswaraju Macha, Prashanthi Mamidi, Sravanthi Manchinella, Achaiah Garlapati, Raghuram Rao Akkinepalli
INDIAN JOURNAL OF PHARMACEUTICAL EDUCATION AND RESEARCH
(2019)
Article
Chemistry, Medicinal
Prabhakar S. Achanta, Sneha Raj, Soyar Horam, Jesu Arockiaraj, Ravi Kumar Bobbala, Raghuram Rao Akkinepally, Mukesh Pasupuleti, Appa Rao V. N. Achanta
DRUG DEVELOPMENT RESEARCH
(2020)
Article
Biochemical Research Methods
Baswaraju Macha, Ravindra Kulkarni, Anil Kumar Garige, Rambabu Palabindala, Raghuramrao Akkinepally, Achaiah Garlapati
Summary: Alzheimer's disease is a common neurodegenerative disease among the elderly population. This study focused on synthesizing new compounds and evaluating their inhibitory activity on cholinesterases, hepatotoxicity, and behavioral studies. The results showed that some compounds exhibited potent inhibitory activity with low hepatotoxicity and good behavioral effects.
COMBINATORIAL CHEMISTRY & HIGH THROUGHPUT SCREENING
(2022)
Article
Pharmacology & Pharmacy
Shivarani Eesam, Jaswanth S. Bhandaru, Raghuram Rao Akkinepally, Ravi Kumar Bobbala
Summary: Cocrystallization was used to enhance the physicochemical properties of the poorly water-soluble drug gliclazide. Among the three different cocrystals tested, GLZ-DNS cocrystals demonstrated significantly improved solubility (6.3 times), degradation (1.5 times), and relative bioavailability (1.8 times) compared to the pure drug.
FUTURE JOURNAL OF PHARMACEUTICAL SCIENCES
(2021)
Article
Pharmacology & Pharmacy
Shivarani Eesam, Jaswanth S. Bhandaru, Chandana Naliganti, Ravi Kumar Bobbala, Raghuram Rao Akkinepally
FUTURE JOURNAL OF PHARMACEUTICAL SCIENCES
(2020)
Article
Pharmacology & Pharmacy
Chandana Naliganti, Chandrasekhar Valupadas, Raghuram Rao Akkinepally, Shivarani Eesam
INDIAN JOURNAL OF PHARMACOLOGY
(2019)
Article
Biochemistry & Molecular Biology
Pran Kishore Deb, Raghuprasad Mailavaram, Balakumar Chandrasekaran, Venkata Rao Kaki, Rajwinder Kaur, Sonja Kachler, Karl-Norbert Klotz, Raghuram Rao Akkinepally
CHEMICAL BIOLOGY & DRUG DESIGN
(2018)
Article
Chemistry, Medicinal
Shuang Mei, Su Jiang, Yuting Wang, Han Jing, Peng Yang, Miao-Miao Niu, Jindong Li, Kai Yuan, Yan Zhang
Summary: This study identifies a dual-targeting peptide, AP-1, that effectively inhibits variants of concern (VOCs) of SARS-CoV-2 without impairing host cell viability. The findings suggest that AP-1 could be a promising broad-spectrum agent for treating emerging VOCs of SARS-CoV-2.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2024)
Article
Chemistry, Medicinal
Hyeonjun Lee, Ju Yeon Lee, Hyunsoo Jang, Hye Young Cho, Minhee Kang, Sang Hyun Bae, Suin Kim, Eunji Kim, Jaebong Jang, Jin Young Kim, Young Ho Jeon
Summary: By using liquid chromatography-tandem mass spectrometry and nuclear magnetic resonance experiments, we identified new chemical moieties that bind to the target sites of the protein of interest, allowing for reversible binding and protein degradation. This method has the potential to expand the application of PROTAC technology.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2024)
Article
Chemistry, Medicinal
Yingying Li, Xiyou Du, Xinru Kong, Yuelin Fang, Zhijing He, Dongzhu Liu, Hang Wu, Jianbo Ji, Xiaoye Yang, Lei Ye, Guangxi Zhai
Summary: This study proposes a novel nanoplatform based on the autophagy cascade to overcome the obstacles in chemo-immunotherapy. The platform combines chemotherapy and starvation therapy to initiate pro-death autophagy and enhance antigen presentation, while also remodeling the immunosuppressive tumor microenvironment. Furthermore, the study discovers a new therapeutic direction for the respiration inhibitor 3-bromopyruvic acid (3BP) in cancer treatment. Overall, this study offers an opportunity to improve antitumor efficacy and boost immune responses.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2024)
Article
Chemistry, Medicinal
Bingsi Wang, Mingxu Ma, Yusen Dai, Pengfei Yu, Liang Ye, Wenyan Wang, Chunjie Sha, Huijie Yang, Yingjie Yang, Yunjing Zhu, Lin Dong, Shujuan Wei, Linlin Wang, Jingwei Tian, Hongbo Wang
Summary: Breast cancer is a common malignant tumor in women, and drug resistance remains a clinical challenge. In this study, a novel compound, G-5b, was developed with potent antagonistic and degradation activities comparable to the current drug fulvestrant. G-5b also showed improved stability and solubility. Mechanistically, G-5b engages the proteasome pathway to degrade ER, inhibiting the ER signaling pathway and inducing apoptosis and cell cycle arrest. In animal models, G-5b exhibited superior pharmacokinetics and pharmacodynamics properties. Overall, G-5b is a promising long-acting SERD worthy of further investigation and optimization.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2024)
Article
Chemistry, Medicinal
Karoline B. Waitman, Larissa C. de Almeida, Marina C. Primi, Jorge A. E. G. Carlos, Claudia Ruiz, Thales Kronenberger, Stefan Laufer, Marcia Ines Goettert, Antti Poso, Sandra V. Vassiliades, Vinicius A. M. de Souza, Monica F. Z. J. Toledo, Neuza M. A. Hassimotto, Michael D. Cameron, Thomas D. Bannister, Leticia Costa-Lotufo, Joa o A. Machado-Neto, Mauricio T. Tavares, Roberto Parise-Filho
Summary: A series of hybrid inhibitors combining pharmacophores of known kinase inhibitors and benzohydroxamate HDAC inhibitors were synthesized and evaluated for their anticancer activity and pharmacokinetic properties. Compounds 4d-f exhibited promising cytotoxicity against hematological cells and moderate activity against solid tumor models. Compound 4d showed potent inhibition of multiple kinase targets and had stable interactions with HDAC and members of the JAK family. These compounds showed selective cytotoxicity with minimal effects on non-tumorigenic cells and favorable pharmacokinetic profiles.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2024)
Article
Chemistry, Medicinal
Michal Sulik, Diana Fontinha, Dietmar Steverding, Szymon Sobczak, Michal Antoszczak, Miguel Prudencio, Adam Huczynski
Summary: This study describes the synthesis of the first-in-class ivermectin derivatives obtained through derivatization of the C13 position, along with the unexpected rearrangement of the macrolide ring. These derivatives show potential for antiparasitic activity and are important for the development of new antiparasitic agents.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2024)
Article
Chemistry, Medicinal
Jun Liu, Qiu-Xian Chen, Wen-Fu Wu, Dong Wang, Si -Yu Zhao, Jia-Hao Li, Yi-Qun Chang, Shao-Gao Zeng, Jia-Yi Hu, Yu-Jie Li, Jia-Xin Du, Shu-Meng Jiao, Hai-Chuan Xiao, Qiang Zhang, Jun Xu, Jian-Fu Zhao, Hai -Bo Zhou, Yong-Heng Wang, Jian Zou, Ping-Hua Sun
Summary: A new anti-infective drug strategy has been discovered to attenuate virulence and modulate inflammation caused by drug-resistant Pseudomonas aeruginosa infections. Compound 5f inhibits biofilm formation, macrophage migration, and inflammatory response induced by P. aeruginosa, showing potential as a novel candidate against drug-resistant infections.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2024)
Article
Chemistry, Medicinal
Liuzeng Chen, Ke Wang, Lingyun Wang, Wei Wang, Lifan Wang, Jia Li, Xiaohan Liu, Mengya Wang, Banfeng Ruan
Summary: In this study, a series of novel anti-inflammatory compounds were designed and synthesized based on the natural product pterostilbene skeleton. Among them, compound 8 showed the highest activity and exhibited its effects through inhibition of pro-inflammatory cytokines by blocking the NF-KB/MAPK signaling pathway. Compound 8 also demonstrated a good relieving effect on acute colitis in mice and showed good safety in acute toxicity experiments.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2024)
Article
Chemistry, Medicinal
Si-Min Liang, Gui-Bin Liang, Hui-Ling Wang, Hong Jiang, Xian-Li Ma, Jian-Hua Wei, Ri-Zhen Huang, Ye Zhang
Summary: A series of novel multi-target antitumor agents were designed, synthesized, and evaluated. Some compounds exhibited significant antitumor activity and one compound showed excellent efficacy, limited toxicity, and low resistance. Further mechanism studies revealed that the compound exerted antitumor effects through multiple pathways.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2024)