Article
Chemistry, Applied
Hongmei Pan, Tong Lu, Xuedan Wu, Chengwen Gu, Naili Tao, Biao Zhang, Ao Wang, Guangmei Chen, Kehua Zhang, Jie Cheng, Jie Jin
Summary: A novel structure of sinomenine isoxazole derivatives was synthesised in six steps from sinomenine hydrochloride and aromatic aldehydes, yielding 19 target compounds. Key intermediates include 4-alkynyl sinomenine and 1,3-dipole, obtained from the reaction of sinomenine hydrochloride with ammonia and substitution reaction with 3-chloropropyne, and from aromatic aldehyde, respectively.
NATURAL PRODUCT RESEARCH
(2021)
Article
Chemistry, Multidisciplinary
Fan Feng, Jing Li, Zhihui Zhang, Jiaxu Fu, Yumin Zhang, Qiang Gu
Summary: An ultrasonic-assisted synthesis method for bis-isoxazole derivatives was developed, resulting in compounds with potent antifungal activity and low minimum inhibitory concentrations against Candida albicans. Compound 6a and 6h showed better antifungal activity compared to the standard drug itraconazole.
CHEMICAL RESEARCH IN CHINESE UNIVERSITIES
(2021)
Article
Chemistry, Organic
Yulin Wang, Cheng Xiong, Jiacheng Zhong, Qingfa Zhou
Summary: A strategy for the 1,3-dipolar cycloaddition of nitrilimines to delta-allenoates has been developed to provide various 1,3,5-trisubstituted pyrazole-4-carboxylates and pyrazole-4-carboxamide derivatives, which have excellent anticancer effects. This protocol exhibits characteristics of good yield, mild reaction condition, facile operation process, and post-processing steps.
Article
Chemistry, Multidisciplinary
Katie Ruffell, Frances R. Smith, Michael T. Green, Simon M. Nicolle, Martyn Inman, William Lewis, Christopher J. Hayes, Christopher J. Moody
Summary: Diazophosphonates, prepared from alpha-ketophosphonates by oxidation, are useful reagents in 1,3-dipolar cycloaddition reactions for synthesizing N-H pyrazoles. They possess stable properties compared to less stable diazoalkanes, and can migrate during the cycloaddition process.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Jian-Bin Lu, Shu-Yuan Liang, Wu-Tao Gui, Zhi-Chao Chen, Wei Du, Ying-Chun Chen
Summary: A relay catalytic protocol utilizing pyrrolidine and palladium catalysis has been developed for the asymmetric synthesis of 1,3-diamine derivatives from 3-substituted 1,3-dienes, sulfuric diamide, and aldehydes. This one-pot, three-component reaction offers the advantages of high atom step economy and operational simplicity, providing an efficient and straightforward access to valuable 1,3-diamines containing quaternary and tertiary stereogenic centers with moderate to good enantioselectivity.
Article
Chemistry, Organic
Geetmani Singh Nongthombam, Romesh Chandra Boruah
Summary: The reaction of 17,17-dichloro-androst-16(E)-chloromethylene with secondary amine base led to substitution products of exocyclic D-ring ketones, while the reaction with alkaline base cleaved the steroidal D-ring to des-D formyl alkyne. The des-D formyl alkyne was then used to prepare D-ring annulated isoxazolo steroid via 1,3-dipolar nitrile oxide cycloaddition reaction.
SYNTHETIC COMMUNICATIONS
(2021)
Article
Chemistry, Physical
Yassine Laamari, Mourad Fawzi, Mouhi Eddine Hachim, Abdoullah Bimoussa, Ali Oubella, El Mostafa Ketatni, Mohamed Saadi, Lahcen El Ammari, My Youssef Ait Itto, Hamid Morjani, Mostafa Khouili, Aziz Auhmani
Summary: In this paper, a novel method for synthesizing thymol derivatives was reported, and the structures of all compounds were identified using spectroscopic techniques. The selectivity of the reactions was determined through theoretical calculations and experimental verification. The electronic interaction properties of the synthesized compounds were analyzed. Additionally, the cytotoxic effects of the compounds were evaluated, and compounds 6b and 6c showed promising anticancer activity against A-549 cell lines.
JOURNAL OF MOLECULAR STRUCTURE
(2024)
Article
Chemistry, Organic
Sona Khodabandlou, Mahnaz Saraei
Summary: A novel series of 3,5-disubstituted isoxazoles bearing kojic acid moiety were synthesized via Cu(I)-catalyzed reaction, showing notable antibacterial and antifungal activities.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS
(2021)
Article
Chemistry, Multidisciplinary
Zhenni Zhao, Zhi Ou, Subarna Jyoti Kalita, Feng Cheng, Qian Huang, Yangyi Gu, Yuhao Wang, Yan Zhao, Yiyong Huang
Summary: This paper reports the first example of a stereoconvergent reaction involving 1,3-dipolar cycloaddition of nitrile oxides and nitrile imines with electron-deficient olefins. The reaction produces compounds with multiple stereogenic centers and exhibits excellent regio- and diastereoselectivities. Through control experiments and calculations, the possibility of thermodynamically stable diastereomers formation during the reaction is ruled out, and a stepwise mechanism is proposed.
CHINESE CHEMICAL LETTERS
(2022)
Article
Chemistry, Organic
Dennis Svatunek, Thomas Hansen, Kendall N. Houk, Trevor A. Hamlin
Summary: The Lewis base F- catalyzes the 1,3-dipolar cycloaddition between CO2 and nitrilimines by activating the nitrilimine and enhancing the rate of the reaction. The strength of primary orbital interactions between the reactants is the origin of this catalysis. The Lewis base activated nitrilimine-F- has high-lying filled FMOs, which promote a rapid nucleophilic attack and overall cycloaddition with CO2.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Sha Li, Yahan Sun, Xiaofang Li, Oskar Smaga, Sebastian Koniarz, Marcin Stepien, Piotr J. Chmielewski
Summary: A 1,3-cycloaddition reaction between 2-(tert-butyl)-8H-isoquinolino[4,3,2-de]phenanthridin-9-ium chloride and Ni-II norcorrole in the presence of base has been demonstrated to yield a family of chiral derivatives fused with pyrrole subunits of the macrocycle. Dehydrogenation of the cycloaddition products leads to dibenzoullazine ortho-fused antiaromatic porphyrinoids.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Mohammed F. F. Radwan, Elghareeb E. E. Elboray, Hemat M. M. Dardeer, Yusuke Kobayashi, Takumi Furuta, Shohei Hamada, Toshifumi Dohi, Moustafa F. F. Aly
Summary: 1,3-Dipolar cycloaddition through in situ generation of azomethine ylide provides a straightforward and critically important sustainable approach for access to diverse pyrrolidine chemical space. Metal-free AcOH-activated 1,3-dipolar cycloaddition protocol was developed to synthesize uncommon pyrrolidine cycloadducts with excellent diastereoselectivity. The reaction mechanism and the key role of AcOH were supported by experimental, theoretical and spectroscopic studies.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Biochemistry & Molecular Biology
Dmitriy D. Karcev, Mariia M. Efremova, Alexander P. Molchanov, Nikolai Rostovskii, Mariya A. Kryukova, Alexander S. Bunev, Dmitry A. Khochenkov
Summary: In this study, new highly functionalized 5-spiroisoxazolidines were synthesized through the 1,3-dipolar cycloaddition reaction, which showed good selectivity. The reversibility of these reactions allows for controlling the diastereoselectivity of cycloaddition. Additionally, the reduction reaction of the obtained adducts provides 1,3-aminoalcohols or spirolactones.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Biochemistry & Molecular Biology
Guipeng Feng, Guoyang Ma, Wenyan Chen, Shaohong Xu, Kaikai Wang, Shaoyan Wang
Summary: The [3 + 2] 1,3-dipolar cycloaddition of C,N-cyclic azomethine imines with allyl alkyl ketones has been achieved, resulting in a range of tetrahydroisoquinoline derivatives with good diastereoselectivities and enantioselectivities. The absolute configuration of the product was determined using quantum electronic circular dichroism calculation and ECD spectrum method.
Article
Chemistry, Organic
Jevgenija Luginina, Martin Linden, Maris Bazulis, Viktors Kumpins, Anatoly Mishnev, Sergey A. Popov, Tatiana S. Golubeva, Siegfried R. Waldvogel, Elvira E. Shults, Maris Turks
Summary: Novel lupane-type triterpenoid-isoxazole conjugates were synthesized by combining electro-organic synthesis and conventional methods. These conjugates exhibited cytostatic properties against various cancer cell lines, while being non-toxic to human fibroblasts.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Medicinal
Kuppi Reddy Gari Divya, Donthamsetty V. Sowmya, Suram Durgamma, Vadlamudi Tharanath, Divi Venkataramana Sai Gopal, Malaka Venkateshwarulu Jyothi Kumar, Chippada Appa Rao, Adivireddy Padmaja, Venkatapuram Padmavathi
MEDICINAL CHEMISTRY RESEARCH
(2017)
Article
Chemistry, Medicinal
Donthamsetty V. Sowmya, Shaik Sharafuddin Basha, Palampalli Uma Maheswari Devi, Yerraguravagari Lavanyalatha, Adivireddy Padmaja, Venkatapuram Padmavathi
MEDICINAL CHEMISTRY RESEARCH
(2017)
Article
Chemistry, Organic
Narendra Babu Kayathi, Donthamsetty V. Sowmya, Padmaja Adivireddy, Padmavathi Venkatapuram
JOURNAL OF HETEROCYCLIC CHEMISTRY
(2018)
Article
Chemistry, Organic
Jyothi Sowdari, Yamini Gudi, Sowmya V. Donthamsetty, Padmavathi Venkatapuram, Padmaja Adivireddy
JOURNAL OF HETEROCYCLIC CHEMISTRY
(2019)
Proceedings Paper
Chemistry, Multidisciplinary
V Manjunath, D. Sowmya, K. Murali Mohan Achari, P. Sandhya, G. Sravya, P. Ananda, M. Krishnaiah
MODERN SYNTHETIC METHODOLOGIES FOR CREATING DRUGS AND FUNCTIONAL MATERIALS (MOSM2019)
(2020)
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)