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Bioorganic Chemistry

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https://www.readbyqxmd.com/read/29153588/azole-hydrazone-derivatives-design-synthesis-in-vitro-biological-evaluation-dual-egfr-her2-inhibitory-activity-cell-cycle-analysis-and-molecular-docking-study-as-anticancer-agents
#1
Madlen B Labib, John N Philoppes, Phoebe F Lamie, Esam R Ahmed
In this research, three series of azole-hydrazone derivatives namely, benzimidazole, benzoxazole and benzothiazole were designed and synthesized. Their structures were confirmed by elemental analysis and spectroscopic techniques. Stereochemical configuration of the synthesized compounds (Z/E) was determined. The new derivatives were tested in vitro against both human breast adenocarcinoma (MCF-7) and human hepatic adenocarcinoma (HepG2) cell lines. The most active compounds 3h (IC50 = 0.067 μM against MCF-7) and 3l (IC50 = 0...
November 15, 2017: Bioorganic Chemistry
https://www.readbyqxmd.com/read/29153589/biocatalytic-hydrolysis-of-chlorinated-nicotinamides-by-a-superior-as-family-amidase-and-its-application-in-enzymatic-production-of-2-chloronicotinic-acid
#2
Ren-Chao Zheng, Jian-Qiang Jin, Zhe-Ming Wu, Xiao-Ling Tang, Li-Qun Jin, Yu-Guo Zheng
2-Chloronicotinic acid (2-CA) is an important building block for a series of agrochemicals and pharmaceuticals. Amidase-catalyzed hydrolysis of 2-chloronicotinamide is one of the most attractive approaches for 2-CA production. However, development of the bioprocess was plagued by low activity of amidase for 2-chloronicotinamide. In this work, an amidase signature (AS) family amidase from Pantoea sp. (Pa-Ami), with superior activity for nicotinamide and its chlorinated derivatives, was exploited and characterized...
November 7, 2017: Bioorganic Chemistry
https://www.readbyqxmd.com/read/29125970/chemical-characterization-of-cytotoxic-indole-acetic-acid-derivative-from-mulberry-fruit-morus-alba-l-against-human-cervical-cancer
#3
Jae Sik Yu, Dahae Lee, Seoung Rak Lee, Jae Wook Lee, Chang-Ik Choi, Tae Su Jang, Ki Sung Kang, Ki Hyun Kim
The fruit of the white mulberry tree (Morus alba L.) is a multiple fruit with a sweet flavor commonly consumed around the world. Chemical investigation of the fruits led to the isolation of two indole acetic acid derivatives (1 -2) including a new compound, which turned out to be an isolation artifact, 3S-(β-D-glucopyranosyloxy)-2,3-dihydro-2-oxo-1H-indole-3-acetic acid butyl ester (1), along with five known compounds (3 -7). Compounds 2 and 7 were newly identified from mulberry fruit. The new isolation artifact (1) exhibited cytotoxic effect on human cervical cancer Hela cells in a dose-dependent manner...
November 7, 2017: Bioorganic Chemistry
https://www.readbyqxmd.com/read/29107839/efficient-one-pot-enzymatic-synthesis-of-dephospho-coenzyme-a
#4
Krishna Sapkota, Faqing Huang
Dephospho coenzyme A (depCoA) is the last intermediate for CoA biosynthesis, and it can be used as a transcription initiator to prepare CoA-linked RNA by in vitro transcription. However, commercially available depCoA is expensive. We hereby describe a simple and efficient enzymatic synthesis of depCoA in a single-step from commercially available and inexpensive oxidized pantethine (Ox-Pan) and ATP. A plasmid (pCoaDAa) was constructed to co-express and co-purify two enzymes pantothenate kinase (PanK/coaA) and phosphopantetheine adenylyltransferase (PPAT/coaD)...
November 3, 2017: Bioorganic Chemistry
https://www.readbyqxmd.com/read/29136525/improving-the-carbonic-anhydrase-inhibition-profile-of-the-sulfamoylphenyl-pharmacophore-by-attachment-of-carbohydrate-moieties
#5
Leonardo E Riafrecha, Silvia Bua, Claudiu T Supuran, Pedro A Colinas
One of the most successful approaches for designing carbonic anhydrase (CA, EC 4.2.1.1) inhibitors was denominated 'the sugar approach'. The sugar approach consists in attaching different carbohydrates to CA inhibiting pharmacophores for modulating the physicochemical properties of these pharmacological agents. In line with this approach, in this paper, we present a new class of C-glycosides incorporating the sulfamoylphenyl moiety. These compounds have been prepared by sulfamoylation of C-glycosyl phenols, which have been synthetized by aldol reaction of glycosyl ketones with the appropriate aromatic aldehydes...
November 2, 2017: Bioorganic Chemistry
https://www.readbyqxmd.com/read/29125971/5-acetyl-6-methyl-4-aryl-3-4-dihydropyrimidin-2-1h-ones-as-potent-urease-inhibitors-synthesis-in-vitro-screening-and-molecular-modeling-study
#6
Shahbaz Shamim, Khalid Mohammed Khan, Uzma Salar, Farman Ali, Muhammad Arif Lodhi, Muhammad Taha, Farman Ali Khan, Sajda Ashraf, Zaheer Ul-Haq, Muhammad Ali, Shahnaz Perveen
5-Acetyl-6-methyl-4-aryl-3,4-dihydropyrimidin-2(1H)-ones 1-43 were synthesized in a "one-pot" three component reaction and structurally characterized by various spectroscopic techniques such as (1)H, (13)C NMR, EI-MS, HREI-MS, and IR. All compounds were evaluated for their in vitro urease inhibitory activity. It is worth mentioning that except derivatives 1, 11, 12, and 14, all were found to be more potent than the standard thiourea (IC50 = 21.25 ± 0.15 µM) and showed their urease inhibitory potential in the range of IC50 = 3...
November 2, 2017: Bioorganic Chemistry
https://www.readbyqxmd.com/read/29102725/structural-modeling-of-osteoarthritis-adamts4-complex-with-its-cognate-inhibitory-protein-timp3-and-rational-derivation-of-cyclic-peptide-inhibitors-from-the-complex-interface-to-target-adamts4
#7
Wei Zhang, Biao Zhong, Chi Zhang, Yukai Wang, Shang Guo, Congfeng Luo, Yulin Zhan
The ADAMTS4 (a disintegrin and metalloproteinase with thrombospondin motifs 4) enzyme is a matrix-associated zinc metalloendopeptidase that plays an essential role in the degradation of cartilage aggrecan in arthritic diseases and has been recognized as one of the most primary targets for therapeutic intervention in osteoarthritis (OA). Here, we reported computational modeling of the atomic-level complex structure of ADAMTS4 with its cognate inhibitory protein TIMP3 based on high-resolution crystal template...
November 2, 2017: Bioorganic Chemistry
https://www.readbyqxmd.com/read/29102724/synthesis-of-benzo-d-imidazo-2-1-b-thiazole-chalcone-conjugates-as-microtubule-targeting-and-apoptosis-inducing-agents
#8
Faria Sultana, Srinivasa Reddy Bonam, V Ganga Reddy, V Lakshma Nayak, Ravikumar Akunuri, Sunitha Rani Routhu, Abdullah Alarifi, M Sampath Kumar Halmuthur, Ahmed Kamal
A series of benzo[d]imidazo[2,1-b]thiazole-chalcone conjugates (5a-aa) were designed, synthesized and evaluated for their cytotoxic potency against a panel of human cancer cell lines like lung (A-549), breast (MDA MB-231), prostrate (DU-145) and colon cancer (HT-29). Preliminary results revealed that some of these conjugates like 5d and 5u exhibited significant antiproliferative effect against human breast cancer (MDA MB-231) with IC50 values of 1.3 and 1.2 µM respectively. To investigate the mechanistic aspects underlying the activity, the detailed biological studies of these promising conjugates (5d and 5u) were carried out on the MDA MB-231 cancer cells...
November 2, 2017: Bioorganic Chemistry
https://www.readbyqxmd.com/read/29102722/hit-discovery-of-4-amino-n-4-3-trifluoromethyl-phenoxy-pyrimidin-5-yl-benzamide-a-novel-egfr-inhibitor-from-a-designed-small-library
#9
Ahmed Elkamhawy, Sora Paik, Ahmed H E Hassan, Yong Sup Lee, Eun Joo Roh
Searching for hit compounds within the huge chemical space resembles the attempt to find a needle in a haystack. Cheminformatics-guided selection of few representative molecules of a rationally designed virtual combinatorial library is a powerful tool to confront this challenge, speed up hit identification and cut off costs. Herein, this approach has been applied to identify hit compounds with novel scaffolds able to inhibit EGFR kinase. From a generated virtual library, six 4-aryloxy-5-aminopyrimidine scaffold-derived compounds were selected, synthesized and evaluated as hit EGFR inhibitors...
November 2, 2017: Bioorganic Chemistry
https://www.readbyqxmd.com/read/29096097/novel-quinoline-3-carboxamides-part-2-design-optimization-and-synthesis-of-quinoline-based-scaffold-as-egfr-inhibitors-with-potent-anticancer-activity
#10
Rasha M Aly, Rabah A T Serya, Amira M El-Motwally, Ahmed Esmat, Safinaz Abbas, Dalal A Abou El Ella
EGFR has a key role in cell growth. Its mutation and overexpression share in epithelial malignancies and tumor growth. Quinazoline and quinoline derivatives are common anticancer intracellular inhibitors of EGFR kinase, and their optimization is an important issue for development of potent targeted anticancer agents. Based on these facts, different strategies were used for optimizing our reported quinoline-3-carboxamide compound III (EGFR IC50 = 5.283 µM and MCF-7 IC50 = 3.46 µM) through different molecular modeling techniques...
October 30, 2017: Bioorganic Chemistry
https://www.readbyqxmd.com/read/29096094/is-the-sudlow-site-i-of-human-serum-albumin-more-generous-to-adopt-prospective-anti-cancer-bioorganic-compound-than-that-of-bovine-a-combined-spectroscopic-and-docking-simulation-approach
#11
Ritika Joshi, Manojkumar Jadhao, Himank Kumar, Sujit Kumar Ghosh
A comparative biophysical study on the individual conformational adaptation embraced by two homologous serum albumins (SA) (bovine and human) towards a potential anticancer bioorganic compound 2-(6-chlorobenzo[d] thiazol-2-yl)-1H-benzo[de] isoquinoline-1,3(2H)- dione (CBIQD) is apparent from the discrimination in binding behavior and the ensuing consequences accomplished by combined in vitro optical spectroscopy, in silico molecular docking and molecular dynamics (MD) simulation. The Sudlow site I of HSA although anion receptive, harbors neutral CBIQD in Sudlow site I (subdomain IIA, close to Trp) of HSA, while in BSA its prefers to snugly fit into Sudlow site II (subdomain IIIA, close to Tyr)...
October 27, 2017: Bioorganic Chemistry
https://www.readbyqxmd.com/read/29102723/synthetic-and-medicinal-perspective-of-thiazolidinones-a-review
#12
REVIEW
Sundeep Kaur Manjal, Ramandeep Kaur, Rohit Bhatia, Kapil Kumar, Virender Singh, Ravi Shankar, Rupinder Kaur, Ravindra K Rawal
In the modern scenario, thiazolidinone scaffold has emerged as a very potent scaffold as per its clinical significance concerned. It has attracted the keen interest of the researchers due to its great diversity in biological activities. Thiazolidinones are the saturated form of thiazole, called thiazolidine with a carbonyl group. The 1,3-thiazolidin-4-ones possess wide range of pharmacological activities such as anti-cancer, anti-diabetic, anti-microbial, anti-viral, anti-inflammatory and anti-convulsant. In the past few years, various newer synthetic approaches have been designed to synthesize diverse scaffolds to explore the various types of biological activities...
October 23, 2017: Bioorganic Chemistry
https://www.readbyqxmd.com/read/29096096/discovery-of-triazole-based-uracil-derivatives-bearing-amide-moieties-as-novel-dipeptidyl-peptidase-iv-inhibitors
#13
Xiaoyan Deng, Li Han, Jinpei Zhou, Huibin Zhang, Qing Li
Dipeptidyl peptidase-IV (DPP-4) is a validated target for T2DM treatment. We previously reported a novel series of triazole-based uracil derivatives bearing aliphatic carboxylic acids with potent DPP-4 inhibitory activities in vitro, but these compounds showed poor hypoglycemic effects in vivo. Herein we further optimized the triazole moiety by amidation of the carboxylic acid to improve in vivo activities. Two series of compounds 3a-f and 4a-g were designed and synthesized. By screening in DPP-4, compound 4c was identified as a potent DPP-4 inhibitor with the IC50 value of 28...
October 23, 2017: Bioorganic Chemistry
https://www.readbyqxmd.com/read/29096095/enzymatic-synthesis-of-1-3-dihydroxyphenylacetoyl-sn-glycerol-optimization-by-response-surface-methodology-and-evaluation-of-its-antioxidant-and-antibacterial-activities
#14
Nadia Kharrat, Imen Aissa, Youssef Dgachi, Fatma Aloui, Fakher Chabchoub, Mohamed Bouaziz, Youssef Gargouri
In this study, the enzymatic synthesis of phenylacetoyl glycerol ester was carried out as a response to the increasing consumer demand for natural compounds. 1,3-dihydroxyphenylacetoyl-sn-Glycerol (1,3-di-HPA-Gly), labeled as "natural" compound with interesting biological properties, has been successfully synthesized for the first time in good yield by a direct esterification of glycerol (Gly) with p-hydroxyphenylacetic acid (p-HPA) using immobilized Candida antarctica lipase as a biocatalyst. Spectroscopic analyses of purified esters showed that the glycerol was mono- or di-esterified on the primary hydroxyl group...
October 23, 2017: Bioorganic Chemistry
https://www.readbyqxmd.com/read/29128707/nitric-oxide-inhibitors-with-a-spiro-diterpenoid-skeleton-from-scutellaria-formosana-structures-no-inhibitory-effects-and-interactions-with-inos
#15
Peixia Wang, Xueyuan Yang, Feng Liu, Yue Liang, Guochen Su, Muhetaer Tuerhong, Da-Qing Jin, Jing Xu, Dongho Lee, Yasushi Ohizumi, Yuanqiang Guo
A phytochemical investigation to obtain new NO inhibitors resulted in the isolation of five new spiro diterpenoids (1 -5) from the aerial parts of Scutellaria formosana. The structures were elucidated on the basis of extensive 1D and 2D NMR spectroscopic data analysis, and the absolute configurations of these compounds were established via comparison of experimental and calculated electronic circular dichroism (ECD) spectra. The nitric oxide (NO) inhibitory effects were evaluated and all of the compounds showed inhibitory effects on lipopolysaccharide-induced NO production in murine microglial BV-2 cells...
October 21, 2017: Bioorganic Chemistry
https://www.readbyqxmd.com/read/29153590/heterocyclic-periphery-in-the-design-of-carbonic-anhydrase-inhibitors-1-2-4-oxadiazol-5-yl-benzenesulfonamides-as-potent-and-selective-inhibitors-of-cytosolic-hca-ii-and-membrane-bound-hca-ix-isoforms
#16
Mikhail Krasavin, Anton Shetnev, Tatyana Sharonova, Sergey Baykov, Tiziano Tuccinardi, Stanislav Kalinin, Andrea Angeli, Claudiu T Supuran
A series of novel aromatic primary sulfonamides decorated with diversely substituted 1,2,4-oxadiazole periphery groups has been prepared using a parallel chemistry approach. The compounds displayed a potent inhibition of cytosolic hCA II and membrane-bound hCA IX isoforms. Due to a different cellular localization of the two target enzymes, the compounds can be viewed as selective inhibition tools for either isoform, depending on the cellular permeability profile. The SAR findings revealed in this study has been well rationalized by docking simulation of the key compounds against the crystal structures of the relevant hCA isoforms...
October 16, 2017: Bioorganic Chemistry
https://www.readbyqxmd.com/read/29078206/new-iridoid-glycosides-from-the-fruits-of-forsythia-suspensa-and-their-hepatoprotective-activities
#17
Si-Yuan Shao, Ya-Nan Yang, Zi-Ming Feng, Jian-Shuang Jiang, Pei-Cheng Zhang
A novel iridoid glycoside trimer named forsydoitriside A (1) and five new iridoid glycosides (2-6) were isolated from the fruits of Forsythia suspensa together with two known compounds (7, 8). These new structures were elucidated by comprehensive spectroscopic data and the comparison of experimental and calculated electronic circular dichroism spectra. Compounds 1-8 were all assayed on acetaminophen-induced HepG2 cell damage. The results exhibited that compounds 2, 3, 5 and 6 possessed strong hepatoprotective activities against the damage in HepG2 cell...
October 16, 2017: Bioorganic Chemistry
https://www.readbyqxmd.com/read/29054071/inactivation-of-bovine-plasma-amine-oxidase-by-1-1-1-trihalo-3-aminopropanes
#18
Jisook Kim, Irene N Lee
In this paper, we report the inactivation of copper containing bovine plasma amine oxidase (BPAO) by a series of saturated alkylamines containing halogen atoms at γ-position, which are 1,1,1-trihalo-3-aminopropane, 1,1,1-trifluoro-2-hydroxy-3-aminopropane, 1,1,1-trichloro-2-hydroxy-3-aminopropane, and 1,1,1-trichloro-2-(2-phenethyloxy)-3-aminopropane. The trihalo-2-hydroxypropylamine analogs exhibited a time-dependent inactivation behavior of BPAO, with 1,1,1-trifluoro-2-hydroxy-3-aminopropane as the most efficient inactivator...
October 16, 2017: Bioorganic Chemistry
https://www.readbyqxmd.com/read/29055857/coumarinyl-pyranopyrimidines-as-new-neuropeptide-s-receptor-antagonists-design-synthesis-homology-and-molecular-docking
#19
Rasha Z Batran, Dina H Dawood, Samia A El-Seginy, Timothy J Maher, Kuljeet S Gugnani, Alejandro N Rondon-Ortiz
In this work, we described the design, synthesis and characterization of a new class of NPSR antagonists bearing the tetracyclic coumarinyl pyranopyrimidine scaffold incorporated with different acyclic and/or heterocyclic moieties. These compounds are highlighted in this study as never being used as NPSR antagonists before which provides a model for the discovery of new bioactive inhibitors that may hold potential for drug development towards anxiety, food, and addiction disorders. Synthetic and medicinal chemistry studies led to the identification of four potent antagonists, compounds 7d, 10, 12 and 13, which were able to significantly inhibit the stimulatory effect of NPS through counteracting the increased intracellular Ca(2+) accumulation...
October 12, 2017: Bioorganic Chemistry
https://www.readbyqxmd.com/read/29031169/3-4-dimethoxybenzohydrazide-derivatives-as-antiulcer-molecular-modeling-and-density-functional-studies
#20
Muhammad Taha, Nor Hadiani Ismail, Hamizah Mohd Zaki, Abdul Wadood, El Hassane Anouar, Syahrul Imran, Bohari M Yamin, Fazal Rahim, Muhammad Ali, Khalid Mohammed Khan
3,4-Dimethoxybenzohydrazide derivatives (1-25) have been synthesized and evaluated for their urease inhibitory potential. Among the series, compounds 2, 3, 4 and 5 with IC50 values 12.61 ± 0.07, 18.24 ± 0.14, 19.22 ± 0.21, and 8.40 ± 0.05 µM, respectively, showed excellent urease inhibitory potentials when compared with standard thiourea (IC50 value 21.40 ± 0.21 µM). Compounds 1, 6, 8, 18, 19 and 20 also showed good to moderate inhibition, while the remaining compounds were found to be completely inactive...
October 7, 2017: Bioorganic Chemistry
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