Bioorganic Chemistry

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Caged xanthones displaying protein tyrosine phosphatase 1B (PTP1B) inhibition from Cratoxylum cochinchinense

Zuo Peng Li, Hyeong-Hwan Lee, Zia Uddin, Yeong Hun Song, more

Bioorganic Chemistry > 2018 > 78 > C > 39-45

Four new caged xanthones (1–4) and two known compounds (5, 6) were isolated from the roots of Cratoxylum cochinchinense, a polyphenol rich plant, collected in China. The structures of the isolated compounds (1–6) were characterized by obtaining their detailed spectroscopic data. In particular, compounds 1 and 6 were fully identified by X-ray crystallographic data. The isolated compounds (1–6) were...

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Design, synthesis and biological evaluation of pyrimidine-based derivatives as VEGFR-2 tyrosine kinase inhibitors

Wuji Sun, Shengquan Hu, Shubiao Fang, Hong Yan

Bioorganic Chemistry > 2018 > 78 > C > 393-405

Vascular endothelial growth factor receptor-2 (VEGFR-2) plays a crucial role in tumor angiogenesis, and inhibition of the VEGFR-2 signaling pathway has already become an attractive approach for cancer therapy. In this study, a novel pyrimidine-based derivative 7j was designed as lead compound, and three series of potent VEGFR-2 inhibitors were synthesized and biologically evaluated against A549 and...

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Synthesis of N′-phenyl-N-hydroxyureas and investigation of their inhibitory activities on human carbonic anhydrases

Murat Bozdag, Fabrizio Carta, Andrea Angeli, Sameh M. Osman, more

Bioorganic Chemistry > 2018 > 78 > C > 1-6

A series of N′-phenyl-N-hydroxyureas has been prepared by reacting hydroxylamine with aromatic isocyanates. These compounds were investigated as inhibitors of human carbonic anhydrases (hCAs, EC 4.2.1.1), considering four physiologically relevant isoforms, the cytosolic isoforms hCA I and II, and tumor associated, transmembrane isoforms hCA IX and XII. The new compounds reported here did not inhibit...

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Novel carbamate derivatives as selective butyrylcholinesterase inhibitors

Marek Bajda, Kamil Łątka, Michalina Hebda, Jakub Jończyk, more

Bioorganic Chemistry > 2018 > 78 > C > 29-38

Selective butyrylcholinesterase inhibitors could be the promising drug candidates, used in treatment of Alzheimer's disease. The study describes the synthesis and biological activity of novel carbamate derivatives with N-phenylpiperazine, N-benzylpiperazine and 4-benzylpiperidine moieties. Biological studies revealed that most of these compounds displayed significant activity against BuChE. Compound...

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Antimicrobial effects of N-benzyloxycarbonyl-S-(2,4-dinitrophenyl) glutathione diesters against chloroquinine sensitive (NF54) and resistant (K1) strains of Plasmodium falciparum

Sylvie Daunes, Claudius D'Silva

Bioorganic Chemistry > 2018 > 78 > C > 115-118

N-Benzyloxycarbony-S-(2,4-dinitrophenyl)glutathione diesters have been investigated for antimalarial activity against chloroquinine sensitive (NF54) and resistant (K1) strains of P. falciparum. Both strains appear equally susceptible to inhibition by compounds 1–4, with an IC₅₀ ∼ 4.92–6.97 μM, consistent with the target of these compounds being the PfMRP transporter. Against the NF54 strain, diester...

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Design, synthesis, in vivo and in silico evaluation of phenacyl triazole hydrazones as new anticonvulsant agents

Leila Dehestani, Nematollah Ahangar, Seyedeh Mahdieh Hashemi, Hamid Irannejad, more

Bioorganic Chemistry > 2018 > 78 > C > 119-129

A series of phenacyl triazole hydrazones 3 have been designed based on the hybridization of (arylalkly)triazole and aroyl hydrazone scaffolds as new anticonvulsant agents. The target compounds 3 were easily synthesized from appropriate phenacyl triazoles and aryl acid hydrazides and characterized by IR, NMR and Mass spectroscopy. The in vivo anticonvulsant evaluation of synthesized compounds by using...

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Synthesis, anti-inflammatory screening, molecular docking, and COX-1,2/-5-LOX inhibition profile of some novel quinoline derivatives

Ibrahim Chaaban, Ola H. Rizk, Tamer M. Ibrahim, Shery S. Henen, more

Bioorganic Chemistry > 2018 > 78 > C > 220-235

New quinoline compounds comprising pyrazole scaffold through different amide linkages were synthesized. The synthesized compounds were evaluated for their anti-inflammatory activity. Eight compounds (5c, 11b,c, 12c, 14a,b, 20a and 21a) were found to exhibit promising anti-inflammatory profiles in acute and sub-acute inflammatory models. They were screened for their ulcerogenic activity and none of...

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Conventional and microwave prompted synthesis, antioxidant, anticholinesterase activity screening and molecular docking studies of new quinolone-triazole hybrids

Arif Mermer, Neslihan Demirbaş, Yakup Şirin, Harun Uslu, more

Bioorganic Chemistry > 2018 > 78 > C > 236-248

The synthesis of ethyl 4-oxo-1,4-dihydroquinoline-3-carboxylates (4, 5) was performed via the reaction of corresponding anilines with diethyl ethoxymethylenemalonate under conventional and also microwave promoted conditions. The treatment of 4 and 5 afforded the corresponding hydrazides (6 and 7). These hydrazides were converted to the corresponding carbo(thio)amides (9a-f and 10a-e) which were then...

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Design, synthesis and evaluation of pterostilbene β-amino alcohol derivatives as multifunctional agents for Alzheimer's disease treatment

Yunxiaozhu Zheng, Xiaoming Qiang, Rui Xu, Qing Song, more

Bioorganic Chemistry > 2018 > 78 > C > 298-306

A series of pterostilbene β-amino alcohol derivatives were designed, synthesized and evaluated as multifunctional agents for the treatment of Alzheimer’s disease (AD). In vitro assays demonstrated that most of the derivatives were selective acetylacholinesterase (AChE) inhibitors with moderate multifunctional properties. Among them, compound 5f exhibited the best inhibitory activity for EeAChE (IC...

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Molecular docking studies and facile synthesis of most potent biologically active N-tert-butyl-4-(4-substituted phenyl)-2-((substituted-2-oxo-2H-chromen-4-yl)methylthio)-6-oxo-1,6-dihydropyrimidine-5-carboxamide hybrids: An approach for microwave-assisted syntheses and biological evaluation

Rakesh R. Chavan, Kallappa M. Hosamani, Badarinath D. Kulkarni, Shrinivas D. Joshi

Bioorganic Chemistry > 2018 > 78 > C > 185-194

An efficient, high yields and rapid synthesis of N-tert-butyl-4-(4-substituted phenyl)-2-((substituted-2-oxo-2H-chromen-4-yl)methylthio)-6-oxo-1,6-dihydropyrimidine-5-carboxamide derivatives (4a–4j) under microwave-irradiation has been described. All the newly synthesized compounds (4a–4j) were characterized by elemental analysis and spectroscopic studies. The synthesised compounds (4a–4j) were evaluated...

article

Chemoenzymatic synthesis of new derivatives of glycyrrhetinic acid with antiviral activity. Molecular docking study

M. Antonela Zígolo, Maximiliano Salinas, Laura Alché, Alicia Baldessari, more

Bioorganic Chemistry > 2018 > 78 > C > 210-219

We present an efficient approach to the synthesis of a series of glycyrrhetinic acid derivatives. Six derivatives, five of them new compounds, were obtained through chemoenzymatic reactions in very good to excellent yield. In order to find the optimal reaction conditions, the influence of various parameters such as enzyme source, nucleophile:substrate ratio, enzyme:substrate ratio, solvent and temperature...

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Synthesis, biological evaluation and molecular docking studies of aminochalcone derivatives as potential anticancer agents by targeting tubulin colchicine binding site

Guangcheng Wang, Zhiyun Peng, Jiebing Zhang, Jie Qiu, more

Bioorganic Chemistry > 2018 > 78 > C > 332-340

A series of aminochalcone derivatives have been synthesized, characterized by HRMS, ¹H NMR and ¹³C NMR and evaluated for their antiproliferative activity against HepG2 and HCT116 human cancer cell lines. The most of new synthesized compounds displayed moderate to potent antiproliferative activity against test cancer cell lines. Among the derivatives, compound 4 displayed potent inhibitory activity...

article

Design, synthesis and biological activity of 4-(4-benzyloxy)phenoxypiperidines as selective and reversible LSD1 inhibitors

Jiayue Xi, Siyuan Xu, Lulu Zhang, Xueyuan Bi, more

Bioorganic Chemistry > 2018 > 78 > C > 7-16

Lysine specific demethylase 1 (LSD1) plays a vital role in epigenetic regulation of gene activation and repression in several human cancers and is recognized as a promising antitumor therapeutic target. In this paper, a series of 4-(4-benzyloxy)phenoxypiperidines were synthesized and evaluated. Among the tested compounds, compound 10d exhibited the potent and reversible inhibitory activity against...

article

Issue TOC

Bioorganic Chemistry > 2018 > 78 > C > ii-xvii

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Anticancer effects of new dibenzenesulfonamides by inducing apoptosis and autophagy pathways and their carbonic anhydrase inhibitory effects on hCA I, hCA II, hCA IX, hCA XII isoenzymes

Halise Inci Gul, Cem Yamali, Merve Bulbuller, Petek Ballar Kirmizibayrak, more

Bioorganic Chemistry > 2018 > 78 > C > 290-297

In this study, new dibenzensulfonamides, 7–9, having the chemical structure 4,4′-(5′-chloro-3′-methyl-5-aryl-3,4-dihydro-1′H,H-[3,4′-bipyrazole]-1′,2-diyl)dibenzenesulfonamide were synthesized in five steps to develop new anticancer drug candidates. Their chemical structures were confirmed by ¹H NMR, ¹³C NMR and HRMS spectra. Cytotoxicities of the dibenzensulfonamides were investigated towards HCC1937,...

article

Potential antioxidant activity of Morita-Baylis-Hillman adducts

Haitham Elleuch, Wafa Mihoubi, Mohamed Mihoubi, Emna Ketata, more

Bioorganic Chemistry > 2018 > 78 > C > 24-28

The wide variety of potent biological activities of Morita-Baylis-Hillman adducts (MBH) encouraged us to synthesize new series of products belonging to this class of compounds, possessing different functionalities and exhibiting potential antioxidant activity.As part of our on-going program on targeting molecules with antioxidant activity, we describe herein different DPPH (2,2-diphenyl-1-picrylhydrazyl)...

article

N-linoleoylamino acids as chiral probes of substrate binding by soybean lipoxygenase-1

Charles H. Clapp, Justin Pachuski, Natasha F. Bassett, Kathleen A. Bishop, more

Bioorganic Chemistry > 2018 > 78 > C > 170-177

Lipoxygenases catalyze the oxygenation of polyunsaturated fatty acids and their derivatives to produce conjugated diene hydroperoxides. Soybean lipoxygenase-1 (SBLO-1) has been the subject of intensive structural and mechanistic study, but the manner in which this enzyme binds substrates is uncertain. Previous studies suggest that the fatty acyl group of the substrate binds in an internal cavity near...

article

Glycosyl glycerides from the aerial parts of Malva verticillata and their chemopreventive effects

Jung-Hwan Ko, Se Min Cho, Sun-Woo Joo, Hyoung-Geun Kim, more

Bioorganic Chemistry > 2018 > 78 > C > 381-392

A new glycosyl glyceride (5) along with twelve known ones (1–4 and 6–13) including two sulfoquinovosyl glycerides (1 and 2) were isolated from the aerial parts of Malva verticillata. Based on several spectroscopic methods, compound 5 was identified to be (2S)-1-O-β-d-galactopyranosyl-3-O-isostearoyl glyceride, and named malvaglycolipid A. Compounds 1 and 2 contained a unique sugar, (6-deoxy-6-sulfo)-α-d-glucopyranose,...

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Editorial Board

Bioorganic Chemistry > 2018 > 78 > C > i

article

New advances in synthesis and clinical aspects of pyrazolo[3,4-d]pyrimidine scaffolds

Khaled R.A. Abdellatif, Rania B. Bakr

Bioorganic Chemistry > 2018 > 78 > C > 341-357

Pyrazolo[3,4-d]pyrimidine ring system constitute an important class of heterocyclic compounds which can serve as a promising scaffold exhibiting many pharmacological activities. This ring system received much attention as it is a purine isostere by replacing imidazole ring in purine with pyrazole moiety in pyrazolo[3,4-d]pyrimidine. Here we concentrate on new advances in the synthesis of this important...

INFONA - science communication portal

Bioorganic Chemistry

Caged xanthones displaying protein tyrosine phosphatase 1B (PTP1B) inhibition from Cratoxylum cochinchinense

Design, synthesis and biological evaluation of pyrimidine-based derivatives as VEGFR-2 tyrosine kinase inhibitors

Synthesis of N′-phenyl-N-hydroxyureas and investigation of their inhibitory activities on human carbonic anhydrases

Novel carbamate derivatives as selective butyrylcholinesterase inhibitors

Antimicrobial effects of N-benzyloxycarbonyl-S-(2,4-dinitrophenyl) glutathione diesters against chloroquinine sensitive (NF54) and resistant (K1) strains of Plasmodium falciparum

Design, synthesis, in vivo and in silico evaluation of phenacyl triazole hydrazones as new anticonvulsant agents

Synthesis, anti-inflammatory screening, molecular docking, and COX-1,2/-5-LOX inhibition profile of some novel quinoline derivatives

Conventional and microwave prompted synthesis, antioxidant, anticholinesterase activity screening and molecular docking studies of new quinolone-triazole hybrids

Design, synthesis and evaluation of pterostilbene β-amino alcohol derivatives as multifunctional agents for Alzheimer's disease treatment

Molecular docking studies and facile synthesis of most potent biologically active N-tert-butyl-4-(4-substituted phenyl)-2-((substituted-2-oxo-2H-chromen-4-yl)methylthio)-6-oxo-1,6-dihydropyrimidine-5-carboxamide hybrids: An approach for microwave-assisted syntheses and biological evaluation

Chemoenzymatic synthesis of new derivatives of glycyrrhetinic acid with antiviral activity. Molecular docking study

Synthesis, biological evaluation and molecular docking studies of aminochalcone derivatives as potential anticancer agents by targeting tubulin colchicine binding site

Design, synthesis and biological activity of 4-(4-benzyloxy)phenoxypiperidines as selective and reversible LSD1 inhibitors

Issue TOC

Anticancer effects of new dibenzenesulfonamides by inducing apoptosis and autophagy pathways and their carbonic anhydrase inhibitory effects on hCA I, hCA II, hCA IX, hCA XII isoenzymes

Potential antioxidant activity of Morita-Baylis-Hillman adducts

N-linoleoylamino acids as chiral probes of substrate binding by soybean lipoxygenase-1

Glycosyl glycerides from the aerial parts of Malva verticillata and their chemopreventive effects

Editorial Board

New advances in synthesis and clinical aspects of pyrazolo[3,4-d]pyrimidine scaffolds

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