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Bioorganic Chemistry

Noah Budin, Erin Higgins, Anthony DiBernardo, Cassidy Raab, Chun Li, Scott Ulrich
The ketone body ester (R)-3-hydroxybutyryl-(R)-3-hydroxybutyrate and its (S,S) enantiomer were prepared in a short, operationally simple synthetic sequence from racemic β-butyrolactone. Enantioselective hydrolysis of β-butyrolactone with immobilized Candida antarctica lipase-B (CAL-B) results in (R)-β-butyrolactone and (S)-β-hydroxybutyric acid, which are easily converted to (R) or (S)-ethyl-3-hydroxybutyrate and reduced to (R) or (S)-1,3 butanediol. Either enantiomer of ethyl-3-hydroxybutyrate and 1,3 butanediol are then coupled, again using CAL-B, to produce the ketone body ester product...
July 13, 2018: Bioorganic Chemistry
Yajie Fu, Bingbing Fan, Hongyue Chen, He Huang, Yi Hu
Based on the screening of biocatalysts and reaction conditions including organic solvent, water content, lipase loading, reaction temperature and time, lipase TLIM exhibited the prominent promiscuity for the Knoevenagel-Michael cascade reactions of 1, 3-diketones with aromatic aldehydes to synthesize xanthone derivatives. This procedure provides satisfactory advantages such as environmental begin, simple work-up, generality, obtaining in excellent yields (80-97%), and potential for recycling of biocatalyst.
July 11, 2018: Bioorganic Chemistry
Asmaa E Kassab, Rasha A Hassan
A series of novel benzotriazole N-acylarylhydrazone hybrids was synthesized according fragment-based design strategy. All the synthesized compounds were evaluated for their anticancer activity against 60 human tumor cell lines by NCI (USA). Five compounds: 3d, 3e, 3f, 3o and 3q exhibited significant to potent anticancer activity at low concentrations. Compound 3q showed the most prominent broad-spectrum anticancer activity against 34 tumor cell lines, with mean growth inhibition percent of 45.80%. It exerted the highest potency against colon HT-29 cell line, with cell growth inhibition 86...
July 10, 2018: Bioorganic Chemistry
Nada M Ghanem, Faten Farouk, Riham F George, Safinaz E S Abbas, Ossama M El-Badry
New imidazo[4,5-b]pyridine derivatives were designed, synthesized and screened for their anticancer activity against breast (MCF-7) and colon (HCT116) cancer cell lines. Nine compounds (I, II, IIIa, IIIb, IV, VI, VIIa, VIII, IX) showed significant activity against MCF-7, while six compounds (I, VIIc, VIIe, VIIf, VIII, IX) elicited a remarkable activity against HCT116. Compounds showing significant anticancer activity revealed remarkable CDK9 inhibitory potential (IC50  = 0.63-1.32 μM) relative to sorafenib (IC50  = 0...
July 6, 2018: Bioorganic Chemistry
Ledong Zhu, Xiaowen Tang, Yanwei Li, Ruiming Zhang, Junjie Wang, Qingzhu Zhang, Wenxing Wang
The lactonization process of Cl-cis,cis-muconate catalyzed by anti-muconate lactonizing enzyme (anti-MLE) was studied theoretically with the aid of a combined quantum mechanics/molecular mechanics (QM/MM) approach. Two elementary processes steps involved in the lactanization process were investigated. The calculated energy barriers agree well with the experimental values. The present work provided the explicit structures of the enolate anion intermediates. The electrostatic influence analysis highlighted residues Arg51, Gln294 and TIP383 for the MLE-Cl-2 system and the residue Asn193 for the MLE-Cl-4 system as the possible mutation targets for rational design of anti-MLE in future enzyme modification...
July 6, 2018: Bioorganic Chemistry
Cristina Lucena-Serrano, Ana Lucena-Serrano, Alicia Rivera, Juan Manuel López-Romero, María Valpuesta, Amelia Díaz
A series of new 1-aryl-6,7-dihydroxy tetrahydroisoquinolines with several substitution patterns in the 1-aryl group at C-1 were prepared in good yields. The influence of each substituent on the affinity and selectivity for D1 and D2 dopaminergic receptors was studied. Moreover, N-alkyl salts of these tetrahydroisoquinolines were used as starting material to synthesize a series of new 1-aryl-7,8-dihydroxy 3-tetrahydrobenzazepines derivatives with electron-withdrawing substituents at C-2 position by the diastereoselective Stevens rearrangement...
July 5, 2018: Bioorganic Chemistry
Guoshun Luo, Zhouyang Qian, Rongmao Qiu, Qidong You, Hua Xiang
Bile acids, initially discovered as endogenous ligands of farnesoid X receptor (FXR), play a central role in the regulation of triglyceride and cholesterol metabolism and have recently emerged as a privileged structure for interacting with nuclear receptors relevant to a large array of metabolic processes. In this paper, phenoxy containing cholic acid derivatives with excellent drug-likeness have been designed, synthesized, and assayed as agents against cholesterol accumulation in Raw264.7 macrophages. The most active compound 14b reduced total cholesterol accumulation in Raw264...
July 5, 2018: Bioorganic Chemistry
Yasser M Omar, Hajjaj H M Abdu-Allah, Samia G Abdel-Moty
Selective inhibition of both cyclooxygenase-2 (COX-2) and 15-lipooxygenase (15-LOX) may provide good strategy for alleviation of inflammatory disorders while minimizing side effects associated with current anti-inflammatory drugs. The present study describes the synthesis, full characterization and biological evaluation of a series of thiadiazole-thiazolidinone hybrids bearing 5-alk/arylidene as dual inhibitors of these enzymes. Our design was based on merging pharmacophores that exhibit portent anti-inflammatory activities in one molecular frame...
July 3, 2018: Bioorganic Chemistry
Nahid Zare, Abedien Zabardasti, Abdelnasser Mohammadi, Farideh Azarbani
A novel Fe(III) Schiff base complex of the [FeL2 (NO3 )2 ]NO3 type where L = 2-((pyridin-4-yl)methyleneamino)-3-aminomaleonitrile was synthesized using the reflux and sonochemical methods and their antibacterial and antifungal activity were evaluated. The nanoparticles of iron oxide (Fe2 O3 ) were obtained from the iron nano-structure complex as a precursor after calcination at 600 ˚C for 3 h. All the synthesized compounds were characterized by various spectroscopic techniques. The results of SEM showed that the morphology of iron nano-structure complex was rod-like while the morphology of the Fe2 O3 nano powder was spherical...
July 3, 2018: Bioorganic Chemistry
Hao Yan, Umesh Bhattarai, Yabin Song, Fu-Sen Liang
miRNAs are key cellular regulators and their dysregulation is associated with many human diseases. They are usually produced locally in a spatiotemporally controlled manner to target mRNAs and regulate gene expression. Thus, developing chemical tools for manipulating miRNA with spatiotemporal precise is critical for studying miRNA. Herein, we designed a strategy to control miRNA biogenesis with light controllable inhibitor targeting the pre-miRNA processing by Dicer. By conjugating two non-inhibiting units, a low affinity Dicer inhibitor and a pre-miRNA binder, through a photocleavable linker, the bifunctional molecule obtained could inhibit miRNA production...
July 2, 2018: Bioorganic Chemistry
Fei Xu, Cai Lu, Qinan Wu, Wei Gu, Jun Chen, Fang Fang, Bo Zhao, Wenjia Du, Min You
Studies on the lipid-regulating effects of alisol compounds are reported that include alisol B, alisol A 24-acetate (24A), alisol A and an alisol B - 24A - alisol A mixture (content ratio = 1:1:1). The effects on the activity of lipoprotein lipase (LPL), a key lipid-modulating enzyme, were studied to investigate the molecular mechanism of lipid-regulating activity of alisols. The effects of alisols on regulating blood lipids and the activities of LPL were determined using a reagent kit method. The structure of LPL was obtained by homology modeling and the interactive mechanism of alisol monomers and the mixture with LPL was investigated by molecular simulation...
July 2, 2018: Bioorganic Chemistry
Marwa A M Sh El-Sharief, Mohamed H El-Naggar, Entesar M Ahmed, Shahenda M El-Messery, Abeer E Mahmoud, Mamdouh M Ali, Lamiaa M Salem, Karima F Mahrous, Mardia T El Sayed
Tetrahydroindolocarbazoles (THICZs) with versatile substituents, have been designed, synthesized, structure characterized, then investigated for their in-vitro anticancer screening, urokinase inhibition (uPA) evaluated, DNA-damage determination was further explored. Compounds 5, 8, 10 and 17 displayed the most promising antitumor activities against the breast cancer cell line as compared to the standard drug, doxorubicin with IC50  = 5.24 ± 0.37, 4.00 ± 0.52, 7.20 ± 0.90 and 9.60 ± 1...
June 30, 2018: Bioorganic Chemistry
Mumtaz Ali, Sardar Ali, Momin Khan, Umer Rashid, Manzoor Ahmad, Ajmal Khan, Ahmed Al-Harrasi, Farhat Ullah, Abdul Latif
A new series of N-acylhydrazone derivatives of 2-mercaptobenzimidazole (2-MBI) has been synthesized through S-alkylation with 1-bromotetradecane and N-alkylation with ethyl-2-chloroacetate. The resulting ester was synthetically modified through hydrazine hydrate to acyl hydrazide which was condensed with aromatic aldehydes to afford the title N-acylhydrazones (4-17). Chemical structures of the newly synthesized compounds have been confirmed through mass, FT-IR and 1 HNMR techniques. In vitro free radical scavenging and α-glucosidase inhibition activities of the compounds were investigated with reference to the standard ascorbic acid and acarbose, respectively...
June 30, 2018: Bioorganic Chemistry
Romeo Romagnoli, Filippo Prencipe, Paola Oliva, Stefania Baraldi, Pier Giovanni Baraldi, Andrea Brancale, Salvatore Ferla, Ernest Hamel, Roberta Bortolozzi, Giampietro Viola
Many natural and synthetic substances are known to interfere with the dynamic assembly of tubulin, preventing the formation of microtubules. In our search for potent and selective antitumor agents, a novel series of 1-(3',4',5'-trimethoxybenzoyl)-5-amino-1,2,4-triazoles were synthesized. The compounds had different heterocycles, including thiophene, furan or the three isomeric pyridines, and they possessed a phenyl ring bearing electron-releasing or electron-withdrawing substituents at the 3-position of the 5-amino-1,2,4-triazole system...
June 30, 2018: Bioorganic Chemistry
Zheng Li, Yueming Chen, Yuhan Zhang, Hongwei Jiang, Yanzhi Liu, Yufang Chen, Luyong Zhang, Hai Qian
The free fatty acid receptor 1 (FFA1) enhances the glucose-stimulated insulin secretion without the risk of hypoglycemia. However, most of FFA1 agonists have a common biphenyl moiety, leading to a relative deprivation in structure types. Herein, we describe the exploration of non-biphenyl scaffold based on the co-crystal structure of FFA1 to increase additional interactions with the lateral residues, which led to the identification of lead compounds 3 and 9. In induced-fit docking study, compound 3 forms an edge-on interaction with Trp150 by slightly rotating the indole ring of Trp150, and compound 9 has additional hydrogen bond and δ-π interactions with Leu135, which demonstrated the feasibility of our design strategy...
June 30, 2018: Bioorganic Chemistry
Maryam Mohammadi-Khanaposhtani, Sepideh Rezaei, Reza Khalifeh, Somaye Imanparast, Mohammad Ali Faramarzi, Saeed Bahadorikhalili, Malihe Safavi, Fatemeh Bandarian, Ensieh Nasli Esfahani, Mohammad Mahdavi, Bagher Larijani
A novel series of acridine linked to thioacetamides 9a-o were synthesized and evaluated for their α-glucosidase inhibitory and cytotoxic activities. All the synthesized compounds exhibited excellent α-glucosidase inhibitory activity in the range of IC50  = 80.0 ± 2.0-383.1 ± 2.0 µM against yeast α-glucosidase, when compared to the standard drug acarbose (IC50  = 750.0 ± 1.5 µM). Among the synthesized compounds, 2-((6-chloro-2-methoxyacridin-9-yl)thio)-N-(p-tolyl) acetamide 9b displayed the highest α-glucosidase inhibitory activity (IC50  = 80...
June 30, 2018: Bioorganic Chemistry
Mengting Liu, Weiguang Sun, Jianping Wang, Yan He, Jinwen Zhang, Fengli Li, Changxing Qi, Hucheng Zhu, Yongbo Xue, Zhengxi Hu, Yonghui Zhang
Three new compounds, including a prenylated tryptophan derivative, luteoride E (1), a butenolide derivative, versicolactone G (2), and a linear aliphatic alcohol, (3E,7E)-4,8-dimethyl-undecane-3,7-diene-1,11-diol (3), together with nine known compounds (4-12), were isolated and identified from a coral-associated fungus Aspergillus terreus. Their structures were elucidated by HRESIMS, one- and two-dimensional NMR analysis, and the absolute configuration of 2 was determined by comparison of its electronic circular dichroism (ECD) spectrum with the literature...
June 27, 2018: Bioorganic Chemistry
Shuang-Gang Ma, Ru-Bing Wang, Wen-Rui Li, Yun-Bao Liu, Jing Qu, Yong Li, Xiao-Jing Wang, Song Xu, Shi-Shan Yu
Two new 3-hydroxy-3-methylglutaryl (HMG) flavanone 7-O-diglycosides, cigranosides A and B (1 and 2), the known naringenin 7-(2''-α-rhamnosyl-6''-(3''''-hydroxy-3''''-methylglutaryl)-glucoside (melitidin, 3), their common biosynthetic precursor flavanone 7-O-diglycoside (naringin, 4), and one known flavone 7-O-diglycoside (rhoifolin, 5) were isolated from the pericarp of Citrus grandis (L.) Osbeck. The structures of these compounds were elucidated by spectroscopic and chemical techniques. The relative ratios and absolute configurations of the C-2 diastereomers of compounds 1, 2 and 4 were determined by online normal-phase HPLC-CD using a Chiralcel column...
June 27, 2018: Bioorganic Chemistry
Ru-Yi Jin, Chu-Yue Zeng, Xu-Hua Liang, Xiao-Hong Sun, Yuan-Fa Liu, Yan-Yan Wang, Sha Zhou
Series of 1,2,4-triazole Schiff bases (2a-2d, 2f-2h and 3a-3h) have been designed and synthesized. The structure of title compounds was confirmed on the basis of their spectral data and elemental analysis. All the target compounds were screened for their in vitro antifungal activity and antibacterial activity. Two of the tested compounds (2a and 2b) exhibited significant antifungal activity against most fungi, especially compound 2a showed better antifungal activity than triadimefon. Meanwhile, the antibacterial activity assay also indicated compound 2a exhibited excellent antibacterial activities comparable to chloramphenicol...
June 25, 2018: Bioorganic Chemistry
Moustafa T Gabr, Mohammed S Abdel-Raziq
Multi-target-directed ligands (MTDLs) centered on β-secretase 1 (BACE-1) inhibition are emerging as innovative therapeutics in addressing the complexity of neurodegenerative diseases. A new series of donepezil analogues was designed, synthesized and evaluated as MTDLs against neurodegenerative diseases. Profiling of donepezil, a potent acetylcholinesterase (hAChE) inhibitor, into BACE-1 inhibition was achieved through introduction of backbone amide linkers to the designed compounds which are capable of hydrogen-bonding with BACE-1 catalytic site...
June 25, 2018: Bioorganic Chemistry
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