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Bioorganic Chemistry

Xue-Gui Liu, Yu-Qiu Sun, Jun Bian, Ting Han, Dan-Dan Yue, Dan-Qi Li, Pin-Yi Gao
Medicago sativa L. is a forage legume plant widely distributed in all continents. Six new triterpenoid saponins, Medicagosides A-F (1-6) and five known ones (7-11) were isolated from M. sativa. Their structures were determined via HRESIMS, 1D and 2D NMR analysis. Biologically, all the isolates displayed neuroprotective activities against H2 O2 -induced damage in SH-SY5Y cells. Among them, compounds 1, 3-5 and 10 exhibited striking neuroprotective activities at 100 μM, restoring cell viability range from 79...
November 13, 2018: Bioorganic Chemistry
Rikang Wang, Chao Zhang, Chaojun Zheng, Huilan Li, Xinshu Xie, Yi Jin, Zhijun Liu, Heru Chen
Incorporation of carbobenzoxy-glycylprolyl (Z-GP) to either α or β position of the hydrazine moiety in procarbazine (Pcb) has been carried on in 5-steps process. The overall yield was 32.7%. The new entity Z-GP-Pcb was confirmed targeting to fibroblast activation protein-α (FAPα). Z-GP-Pcb may be hydrolyzed by either isolated rhFAPα or tumor homogenate. It was shown far less cytotoxicity against NCI-H460 cell line than Pcb. Z-GP-Pcb was displayed the potency to reduce spermatoxcity in H22-bearing mice...
November 12, 2018: Bioorganic Chemistry
Soon Young Shin, Junho Lee, Jihyun Park, Youngshim Lee, Seunghyun Ahn, Ji Hye Lee, Dongsoo Koh, Young Han Lee, Yoongho Lim
A moderate elevation in reactive oxygen species (ROS) levels can generally be controlled in normal cells, but may lead to death of cancer cells as the ROS level in cancer cells is already elevated. Therefore, a ROS-generating compound can act as a selective chemotherapeutic agent for cancer cells that does not affect normal cells. In our previous study, a compound containing a Michael acceptor was selectively cytotoxic to cancer cells without affecting normal cells; therefore, we designed and synthesized 26 compounds containing a Michael acceptor...
November 10, 2018: Bioorganic Chemistry
Ewa Mironiuk-Puchalska, Włodzimierz Buchowicz, Piotr Grześkowiak, Patrycja Wińska, Monika Wielechowska, Olena Karatsai, Maria Jolanta Rędowicz, Maria Bretner, Mariola Koszytkowska-Stawińska
The 1H-1,2,3-triazole-originated derivatives of willardiine were obtained by: (i) construction of the 1H-1,2,3-triazole ring in 1,3-dipolar cycloaddition of the uracil-derived azides and the carboxylate-bearing alkynes or α-acylphosphorus ylide, or (ii) N-alkylation of the uracil derivative with the 1H-1,2,3-triazole-4-carboxylate-derived mesylate. The latter method offered: (i) reproducible results, (ii) a significant reduction of amounts of auxiliary materials, (iii) reduction in wastes and (iv) reduction in a number of manual operations required for obtaining the reaction product...
November 7, 2018: Bioorganic Chemistry
Juan Wang, Wei Li, Jingfang Qin, Li Wang, Shenqi Wei, Huang Tang
A series of 6-substituted azaanthraquinone derivatives have been designed, synthesized, and their anti-inflammatory activities, antiaggregation effects on β-amyloid proteins, anticholinesterase and neuroprotective activity were tested. The new derivatives strongly suppressed NO and iNOS production and modulate the production of cytokines by decreasing TNF-a, IL-1β and IL-6 formation in lipopolysaccharide (LPS)-activated RAW 264.7 macrophages. Meanwhile, the derivatives exhibited a significant in vitro inhibitory activity toward the self-induced Aβ aggregation...
November 7, 2018: Bioorganic Chemistry
Koichi Takao, Yuka Kubota, Hitoshi Kamauchi, Yoshiaki Sugita
A series of eighteen pyrano[4,3-b][1]benzopyranone derivatives (1a-9b) were synthesized, and structure-activity relationships of their monoamine oxidase (MAO) A and B, acetylcholinesterase (AChE), and butyrylcholinesterase (BChE) inhibitory activities were evaluated. Most of the synthesized compounds exhibited weak inhibitory activity toward MAO-A, whereas compounds 2a, 2b, 4a, 4b, 5a, 5b, 6a, 6b, 8a and 8b showed potent inhibitory activities toward MAO-B. Intriguingly, compounds 5a, 5b, and 8a showed inhibitory activities comparable to pargylin, used as a positive control for MAO-B...
November 3, 2018: Bioorganic Chemistry
Abdullah Biçer, Parham Taslimi, Gül Yakalı, Ilhami Gülçin, Mehmet Serdar Gültekin, Günseli Turgut Cin
In this study, a series of novel bis-thiomethylcyclohexanone compounds (3a-3j) were synthesized by the addition of thio-Michael to the bis-chalcones under mild reaction conditions. The bis-thiomethylcyclohexanone derivatives (bis-sulfides) were characterized by 1 H NMR, 13 C NMR, FTIR and elemental analysis techniques. Furthermore, the molecular and crystal structures of 3h, 3i and 3j compounds were determined by single crystal X-ray diffraction studies. In this study, X-ray crystallography provided an alternative and often-complementary means for elucidating functional groups at the enzyme inhibitory site...
November 3, 2018: Bioorganic Chemistry
Jia Xu, Ye Yuan, Ruining Zhang, Yanhui Song, Tianzhuo Sui, Jiaqi Wang, Chonghan Wang, Yujia Chen, Shuwen Guan, Liping Wang
Alzheimer's disease (AD) is a progressive neurodegenerative brain disease and is the most common cause of dementia in the elderly. The main hallmark of AD is the deposition of insoluble amyloid (Aβ) outside the neuron, leading to amyloid plaques and neurofibrillary tangles in the brain. Deuterohemin-Ala-His-Thr-Val-Glu-Lys (DhHP-6), a novel porphyrin-peptide, has both microperoxidase activity and cell permeability. In the present study, DhHP-6 efficiently inhibited the aggregation of Aβ and reduced the β-sheet percentage of Aβ from 89...
November 3, 2018: Bioorganic Chemistry
Hasan Küçükbay, Nesrin Buğday, F Zehra Küçükbay, Emanuela Berrino, Gianluca Bartolucci, Sonia Del Prete, Clemente Capasso, Claudiu T Supuran
Thirty novel sulfonamide derivatives incorporating dipeptide were synthesized by facile acylation through benzotriazole mediated reactions and their structures were identified by 1 H NMR, 13 C NMR, MS and FT-IR spectroscopic techniques and elemental analysis. The carbonic anhydrase (CA, EC inhibitory activity of the new compounds was assessed against four human (h) isoforms, hCA I, hCA II, hCA IV and hCA XII. Most of the synthesized compounds showed excellent in vitro carbonic anhydrase inhibitory properties comparable to those of the clinically used drug acetazolamide (AAZ)...
November 3, 2018: Bioorganic Chemistry
Ladislav Janovec, Jana Janočková, Mária Matejová, Eva Konkoľová, Helena Paulíková, Daniela Lichancová, Lenka Júnošová, Slávka Hamuľaková, Ján Imrich, Mária Kožurková
Nonsteroidal anti-inflammatory drugs (NSAIDs) are the most widely used drugs in the world but some NSAIDs such as diclofenac and tolfenamic acid display levels of cytotoxicity, an effect which has been attributed to the presence of diphenylamine contained in their structures. A novel series of diphenylamine derivatives were synthetised and evaluated for their cytotoxic activities and proliferation inhibition. The most active compounds in the cytotoxicity tests were derivative 6g with an IC50 value of 2.5 ± 1...
November 2, 2018: Bioorganic Chemistry
Xiaobo Zhou, Yuan Qing Qu, Zhiyuan Zheng, Betty Yuen Kwan Law, Simon Wing Fai Mok, Zhi-Hong Jiang, Vincent Kam Wai Wong, Li-Ping Bai
Eleven dauricine derivatives were synthesized and evaluated for their anti-cancer effect in different cancer cells and their autophagic activity in HeLa model cell. Among these newly synthesized compounds, carbamates 2a, 2b, carbonyl ester 3a and sulfonyl ester 4a exhibited potent cytotoxic effects on tested cancer cells with IC50 values ranged from 2.72 to 12.53 μM, which were more potent than that of dauricine (higher than 15.53 μM). The above four derivatives are validated to induce autophagy-dependent cell death in HeLa cancer cells...
November 2, 2018: Bioorganic Chemistry
Samar H Abbas, Amer Ali Abd El-Hafeez, Mai E Shoman, Monica M Montano, Heba A Hassan
A series of quinoline-chalcone hybrids was designed as potential anti-cancer agents, synthesized and evaluated. Different cytotoxic assays revealed that compounds experienced promising activity. Compounds 9i and 9j were the most potent against all the cell lines tested with IC50  = 1.91-5.29 µM against A549 and K-562 cells. Mechanistically, 9i and 9j induced G2 /M cell cycle arrest and apoptosis in both A549 and K562 cells. Moreover, all PI3K isoforms were inhibited non selectively with IC50 s of 52-473 nM when tested against the two mentioned compounds with 9i being most potent against PI3K-γ (IC50  = 52 nM)...
November 2, 2018: Bioorganic Chemistry
Nevine M Y Elsayed, Rabah A T Serya, Mai F Tolba, Marawan Ahmed, Khaled Barakat, Dalal A Abou El Ella, Khaled A M Abouzid
VEGFR-2 has a pivotal role in promoting cancer angiogenesis. Herein, two series of novel indazole-based derivatives were designed, synthesized and evaluated for their in vitro inhibitory action against VEGFR-2 kinase enzyme. The second series 11a-e exhibited better potency than the first one 7a-d and 8a-f. Compounds 11b, 11c and 11e exhibited the most potent action, with IC50 of 5.4 nM, 5.6 nM and 7 nM, respectively. As a measure of cellular VEGFR-2 inhibition, compounds 11b and 11c showed strong inhibition of human umbilical vein endothelial cells (HUVEC) proliferation with 80% and 99...
November 2, 2018: Bioorganic Chemistry
Mohamed Teleb, Ola H Rizk, Fang-Xiong Zhang, Frank R Fronczek, Gerald W Zamponi, Hesham Fahmy
New dihydropyrimidines bearing various lipophilic pharmacophores and functionalities at position 3 were designed and synthesized. The basic framework of the new compounds was designed to maintain the main structural requirements for calcium channel blocking activity of the known dihydropyridines and dihydropyrimidines calcium channel blockers. The newly synthesized compounds were evaluated as antagonists for CaV 1.2 and CaV 3.2 using the whole-cell patch clamp technique. Seven compounds (4b, 4c, 6c, 9, 13c, 13e and 17b) showed promising dual calcium channel blocking activity and three compounds (13b, 14b and 17a) were selective against Cav3...
November 1, 2018: Bioorganic Chemistry
Tomáš Klunda, Sergej Šesták, Juraj Kóňa, Monika Poláková
Inhibition of the biosynthesis of complex N-glycans in the Golgi apparatus is one of alternative ways to suppress growth of tumor tissue. Eight N-benzyl substituted 1,4-imino-l-lyxitols with basic functional groups (amine, amidine, guanidine), hydroxyl and fluoro groups were prepared, optimized their syntheses and tested for their ability to inhibit several α-mannosides from the GH family 38 (GMIIb, LManII and JBMan) as models for human Golgi and lysosomal α-mannoside II. All compounds were found to be selective inhibitors of GMIIb...
October 31, 2018: Bioorganic Chemistry
Morteza Ashooriha, Mehdi Khoshneviszadeh, Mahsima Khoshneviszadeh, Seyed Ershad Moradi, Alireza Rafiei, Mostafa Kardan, Saeed Emami
A series of kojic acid-derived compounds 6a-p bearing aryloxymethyl-1H-1,2,3-triazol-1-yl moiety were designed by modifying primary alcoholic group of kojic acid as tyrosinase inhibitors. The target compounds 6a-p were synthesized via click reaction. All compounds showed very potent anti-tyrosinase activity (IC50 s = 0.06-6.80 µM), being superior to reference drug, kojic acid. In particular, the naphthyloxy analogs 6o and 6p were found to be 31-155 times more potent than kojic acid. The metal-binding study of selected compound 6o revealed that the prototype compound possesses metal-chelating ability, particularly with Cu2+ ions...
October 31, 2018: Bioorganic Chemistry
Halima Meriem Issaadi, József Csábi, Tusty-Jiuan Hsieh, Tamás Gáti, Gábor Tóth, Attila Hunyadi
Phytoecdysteroids exert their non-hormonal anabolic and adaptogenic effects in mammals, including humans, through a partially revealed mechanism of action involving the activation of protein kinase B (Akt). We have recently found that poststerone, a side-chain cleaved in vivo metabolite of 20-hydroxyecdysone, exerts potent anabolic activity in rats. Here we report the semi-synthetic preparation of a series of side-chain cleaved ecdysteroids and their activity on the Akt phosphorylation in murine skeletal muscle cells...
October 31, 2018: Bioorganic Chemistry
Sandra Prasch, Alexandra G Duran, Nuria Chinchilla, José M G Molinillo, Francisco A Macías, Franz Bucar
Capsaicinoids are reported to have a bunch of promising pharmacological activities, among them antibacterial effects against various strains of bacteria. In this study the effect on efflux pumps of mycobacteria was investigated. The importance of efflux pumps, and the inhibition of these, is rising due to their involvement in antibiotic resistance development. In order to draw structure and activity relationships we tested natural and synthetical capsaicinoids as well as synthetical capsinoids. In an accumulation assay these compounds were evaluated for their ability to accumulate ethidium bromide into mycobacterial cells, a well-known substrate for efflux pumps...
October 30, 2018: Bioorganic Chemistry
Rafat M Mohareb, Eman M Samir, Peter A Halim
Heterocyclization of steroids were reported to give biologically active products where ring D modification occured. Estrone (1) was used as a template to develop new heterocyclic compounds. Ring D modification of 1 through its reaction with cyanoacetylhydrazine and elemental sulfur gave the thiophene derivative 3. The latter compound reacted with acetophenone derivatives 4a-c to give the hydrazide-hydrazone derivatives 5a-c, respectively. In addition, compound 3 formed thiazole derivatives through its first reaction with phenylisothiocyanate to give the thiourea derivative 9 followed by the reaction of the later with α-halocarbonyl compounds...
October 30, 2018: Bioorganic Chemistry
Arezoo Rastegari, Hamid Nadri, Mohammad Mahdavi, Alireza Moradi, Seyedeh Sara Mirfazli, Najmeh Edraki, Farshad Homayouni Moghadam, Bagher Larijani, Tahmineh Akbarzadeh, Mina Saeedi
Alzheimer's disease (AD) is a well-known neurodegenerative disorder affecting millions of old people worldwide and the corresponding epidemiological data highlights the significance of the disease. As AD is a multifactorial illness, various single-target directed drugs that have reached clinical trials have failed. Therefore, various factors associated with outset of AD have been considered in targeted drug discovery and development. In this work, a wide range of 1,2,3-triazole-chromenone carboxamides were designed, synthesized, and evaluated for their cholinesterase inhibitory activity...
October 30, 2018: Bioorganic Chemistry
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