Abstract：
:Enantioselective synthesis of functionalized cyclic allylic alcohols via kinetic resolution in transesterifcation with different lipase enzymes has been developed. The influence of the enzymes and temperature activity was studied. By determination of ideal reaction conditions, byproduct formation is minimized; this made it possible to prepare enantiomerically enriched allylic alcohols in high ee's and good yields. Enantiomerically enriched allylic alcohols were used for enantiomerically enriched oxazolidinone synthesis. Using benzoate as a leaving group means that 1 mol % of potassium osmate is necessary and can be obtained high yields 98%. Inhibitory activities of enantiomerically enriched oxazolidinones (8, 10 and 12) were tested against human carbonic anhydrase I and II isoenzymes (hCA I and hCA II), acetylcholinesterase (AChE), and α-glycosidase (α-Gly) enzymes. These enantiomerically enriched oxazolidinones derivatives had Ki values in the range of 11.6 ± 2.1-66.4 ± 22.7 nM for hCA I, 34.1 ± 6.7-45.2 ± 12.9 nM for hCA II, 16.5 ± 2.9 to 35.6 ± 13.9 for AChE, and 22.3 ± 6.0-70.9 ± 9.9 nM for α-glycosidase enzyme. Moreover, they had high binding affinity with -5.767, -6.568, -9.014, and -8.563 kcal/mol for hCA I, hCA II, AChE and α-glycosidase enzyme, respectively. These results strongly supported the promising nature of the enantiomerically enriched oxazolidinones as selective hCA, AChE, and α-glycosidase inhibitors. Overall, due to these derivatives' inhibitory potential on the tested enzymes, they are promising drug candidates for the treatment of diseases like glaucoma, leukemia, epilepsy; Alzheimer's disease; type-2 diabetes mellitus that are associated with high enzymatic activity of CA, AChE, and α-glycosidase.
journal_name
Bioorg Chemjournal_title
Bioorganic chemistryauthors
Atmaca U,Kaya R,Karaman HS,Çelik M,Gülçin İdoi
10.1016/j.bioorg.2019.102980subject
Has Abstractpub_date
2019-07-01 00:00:00pages
102980eissn
0045-2068issn
1090-2120pii
S0045-2068(19)30419-5journal_volume
88pub_type
杂志文章abstract：:HDAC inhibitors and BRD4 inhibitors were considered to be potent anti-cancer agents. Recent studies have demonstrated that HDAC and BRD4 participate in the regulation of some signal paths like PI3K-AKT. In this work, a series of indole derivatives that combine the inhibitory activities of BRD4 and HDAC into one molecu...
journal_title：Bioorganic chemistry
pub_type： 杂志文章
doi：10.1016/j.bioorg.2018.12.011
更新日期：2019-03-01 00:00:00
abstract：:The first enzyme in the shikimic acid biosynthetic pathway, 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase (DAH7PS), varies significantly in size and complexity in the bacteria and plants that express it. The DAH7PS from the archaebacterium Aeropyrum pernix (DAH7PS(Ap)) is among the smallest and least complex of...
journal_title：Bioorganic chemistry
pub_type： 杂志文章
doi：10.1016/j.bioorg.2011.09.002
更新日期：2012-02-01 00:00:00
abstract：:To discover new natural-product-based pesticides, we structurally modified andrographolide, a labdane diterpenoid isolated from Andrographis paniculata, and stereoselectively prepared a series of 12α-(substituted)benzylamino-14-deoxyandrographolide derivatives (I-V). Three-dimensional structures of compounds 3c, 3d, I...
journal_title：Bioorganic chemistry
pub_type： 杂志文章
doi：10.1016/j.bioorg.2019.01.020
更新日期：2019-05-01 00:00:00
abstract：:With the rapid development of nanotechnology, much has been anticipated with silver nanoparticles (AgNPs) due to their extensive industrial and commercial applications. However, it has raised concerns over environmental safety and human health effects. In this study, AgNPs were bio-fabricated using aqueous extract of ...
journal_title：Bioorganic chemistry
pub_type： 杂志文章
doi：10.1016/j.bioorg.2020.104535
更新日期：2020-12-11 00:00:00
abstract：:A series of 4-imidazolylflavans having a variety of substituents on the 2-phenyl ring was synthesized and investigated for their inhibitory effect against aromatase. Structure-activity relationships of these compounds were determined. An additional chlorine atom or a cyano group at the 4' position did not enhance arom...
journal_title：Bioorganic chemistry
pub_type： 杂志文章
doi：10.1016/j.bioorg.2004.06.008
更新日期：2004-12-01 00:00:00
abstract：:A phytochemical study to obtain new nitric oxide (NO) inhibitors resulted in the isolation of five new withanolides from the whole plants of Physalis peruviana. The structures were determined on the basis of extensive NMR spectroscopic data analysis as well as the time-dependent density functional theory (TDDFT) elect...
journal_title：Bioorganic chemistry
pub_type： 杂志文章
doi：10.1016/j.bioorg.2019.03.051
更新日期：2019-06-01 00:00:00
abstract：:Chemical investigation of the roots of Croton crassifolius led to the isolation of five pyran-2-one derivatives, including two brand new compounds (1-2), one new natural product (3) and two known compounds (4-5). Their structures and absolute configurations were established by spectroscopic analyses as well as compari...
journal_title：Bioorganic chemistry
pub_type： 杂志文章
doi：10.1016/j.bioorg.2018.05.020
更新日期：2018-09-01 00:00:00
abstract：:With the aim to discover novel, efficient and selective inhibitors of human alkaline phosphatase and nucleotide pyrophosphatase enzymes, two new series of pyrazolyl pyrimidinetriones (PPTs) (6a-g) and thioxopyrimidinediones (PTPs) (6h-n) were synthesized in good chemical yields using Knoevenagel condensation reaction ...
journal_title：Bioorganic chemistry
pub_type： 杂志文章
doi：10.1016/j.bioorg.2019.03.067
更新日期：2019-07-01 00:00:00
abstract：:Alkyl ester prodrugs are well known to be bioconverted by carboxylesterases, particularly in rodents' by first-pass metabolism in the systemic circulation and liver. However, the bioconversion of structurally more complex esters with polar functional groups is less well understood, especially in humans. Therefore, it ...
journal_title：Bioorganic chemistry
pub_type： 杂志文章
doi：10.1016/j.bioorg.2018.09.018
更新日期：2018-12-01 00:00:00
abstract：:A new ellagitannin, agritannin (1), a new flavone glycoside, agriflavone (2), and another flavone glycoside with spectroscopic data reported for the first time, kaempferol-3-O-[(S)-3-hydroxy-3-methylglutaryl (1→6)]-β-d-glucoside (3), along with 16 known compounds were isolated from the aerial parts of Agrimonia pilosa...
journal_title：Bioorganic chemistry
pub_type： 杂志文章
doi：10.1016/j.bioorg.2017.04.017
更新日期：2017-06-01 00:00:00
abstract：:There is much interest in the use of phytoestrogens such as coumestrol in breast cancer intervention due to their antiestrogenic activity and multiple modes of tumor cell death. However, the clear beneficial effects of naturally occurring estrogen mimetic coumestrol remain controversial due to experimental evidence th...
journal_title：Bioorganic chemistry
pub_type： 杂志文章
doi：10.1016/j.bioorg.2018.12.024
更新日期：2019-04-01 00:00:00
abstract：:A new series of 2-(4-aminobenzosulfonyl)-5H-benzo[b]carbazole-6,11-dione derivatives, which has not been reported yet, has been synthesized from 1,4-naphthoquinone and 4-aminophenylsulfone involving an Michael addition, benzoylation and Pd catalyzed coupling. This set of compounds has been evaluated for in vitro cytot...
journal_title：Bioorganic chemistry
pub_type： 杂志文章
doi：10.1016/j.bioorg.2014.01.002
更新日期：2014-04-01 00:00:00
abstract：:The development of vasorelaxant as the antihypertensive drug is important as it produces a rapid and direct relaxation effect on the blood vessel muscles. Resveratrol (RV), as the most widely studied stilbenoid and the lead compound, inducing the excellent vasorelaxation effect through the multiple signalling pathways...
journal_title：Bioorganic chemistry
pub_type： 杂志文章
doi：10.1016/j.bioorg.2020.104239
更新日期：2020-11-01 00:00:00
abstract：:Pulmonary tuberculosis (TB) is an infectious disease caused by Mycobacterium tuberculosis (MTB) and still remains one of the foremost fatal infectious diseases, infecting nearly a third of the worldwide population. The emergencies of multidrug-resistant and extensively drug-resistant tuberculosis (MDR and XDR-TB) prom...
journal_title：Bioorganic chemistry
pub_type： 杂志文章,评审
doi：10.1016/j.bioorg.2019.102969
更新日期：2019-07-01 00:00:00
abstract：:Analkali tolerant α-l-rhamnosidase has been purified to homogeneity from the culture filtrate of a new fungal strain, Fusarium moniliforme MTCC-2088, using concentration by ultrafiltration and cation exchange chromatography on CM cellulose column. The molecular mass of the purified enzyme has been found to be 36.0 kDa...
journal_title：Bioorganic chemistry
pub_type： 杂志文章
doi：10.1016/j.bioorg.2018.11.027
更新日期：2019-03-01 00:00:00
abstract：:Novel benzothiazole-based compounds were designed and synthesized as potential antimicrobial agents with dual DNA gyrase/topoisomerase IV inhibitory activity. The structures of the newly synthesized compounds were established on the basis of spectral (IR, NMR, MS) and elemental analyses. Most of the studied compounds ...
journal_title：Bioorganic chemistry
pub_type： 杂志文章
doi：10.1016/j.bioorg.2019.103437
更新日期：2020-01-01 00:00:00
abstract：:In an effort to discover novel inhibitors of M. tuberculosis Caseinolytic proteases (ClpP1P2), a combination strategy of virtual high-throughput screening and in vitro assay was employed and a new pyrrole compound, 1-(2-chloro-6-fluorobenzyl)-2, 5-dimethyl-4-((phenethylamino)methyl)-1H-pyrrole-3-carboxylate was found ...
journal_title：Bioorganic chemistry
pub_type： 杂志文章
doi：10.1016/j.bioorg.2018.06.004
更新日期：2018-10-01 00:00:00
abstract：:2-Epi-jaspine B is an isomer of the natural product jaspine B and shows certain selectivity for SphK1 and potent antitumor activity. Based on the crystal structure of SphK1, we transformed the structure of 2-epi-jaspine B and modified the hydrophobic side chain to obtain a series of 2-epi-jaspine B analogs. The MTT as...
journal_title：Bioorganic chemistry
pub_type： 杂志文章
doi：10.1016/j.bioorg.2019.103369
更新日期：2020-05-01 00:00:00
abstract：:A new series of triazolopyrimidines and thiazolopyrimidine hydrobromides was designed and prepared as topoisomerase II inhibitors. Screening of all synthesized compounds was carried out by the National Cancer Institute (NCI) of USA. Activity against 60 human cancer cell lines representing different cancer types was de...
journal_title：Bioorganic chemistry
pub_type： 杂志文章
doi：10.1016/j.bioorg.2020.104134
更新日期：2020-10-01 00:00:00
abstract：:A series of thirteen novel 2,4-thiazolidinedione derivatives were synthesized through three step reaction procedure. The title compounds were synthesized by Knoevenagel condensation at the 5th position of the 2,4-thiazolidinedione ring. Various physicochemical and spectral studies were conducted to characterize the sy...
journal_title：Bioorganic chemistry
pub_type： 杂志文章
doi：10.1016/j.bioorg.2019.102993
更新日期：2019-08-01 00:00:00
abstract：:Biological membranes are one of the most important elements of living cells determining their permeability to the active compounds. Still, little is known about the drug-membrane interactions in terms of pharmacological properties of potential drugs. Chemoprevention based on natural compounds is becoming a strong tren...
journal_title：Bioorganic chemistry
pub_type： 杂志文章
doi：10.1016/j.bioorg.2019.103242
更新日期：2019-11-01 00:00:00
abstract：:Plant compounds have been identified as new drug prototypes. In this line, this work aimed to isolate the indole alkaloid affinisine from Tabernaemontana catharinensis and test its antitumor activity. The alkaloid was isolated by silica gel open column chromatography from the ethanolic extract of the stem of T. cathar...
journal_title：Bioorganic chemistry
pub_type： 杂志文章
doi：10.1016/j.bioorg.2019.103079
更新日期：2019-09-01 00:00:00
abstract：:We present efficient synthesis of isomeric types of angularly fused diquinothiazines in the reactions of 2,2'-dichloro-3,3'-diquinolinyl disulfide and diquinodithiin with 3-, 5-, 6- and 8-aminoquinolines. The pentacyclic diquinothiazine ring systems were identified as diquino[3,2-b;3',4'-e][1,4]thiazine, diquino[3,2-b...
journal_title：Bioorganic chemistry
pub_type： 杂志文章
doi：10.1016/j.bioorg.2019.04.005
更新日期：2019-06-01 00:00:00
abstract：:We recently reported that esterification of 5'-AMP with N-acetyl amino acids proceeds with a preference for D-amino acids, and the D/L ratio in products declines as the hydrophobicity of the amino acid declines. Using one amino acid, Ac-Val, we now show that esterification of all four nucleotides proceeds with a pref...
journal_title：Bioorganic chemistry
pub_type： 杂志文章
doi：10.1016/0045-2068(92)90019-y
更新日期：1992-01-01 00:00:00
abstract：:A series of iminothiazolines (4a-j) featuring 2,4,5-trichlorophenyl moiety and aroyl/heteroaroyl substituents has been prepared from readily accessible thioureas. In-vitro screening against glucosidase enzymes showed highly specific inhibition of α-glucosidase with a marked dependence of the potency upon the nature of...
journal_title：Bioorganic chemistry
pub_type： 杂志文章
doi：10.1016/j.bioorg.2017.07.012
更新日期：2017-10-01 00:00:00
abstract：:Tyrosinase inhibitors have become increasingly important as whitening agents and for the treatment of pigmentary disorders. In this study, the synthesis of kojic acid derivatives having 2-substituted-3-hydroxy-6-hyroxymethyl/chloromethyl/methyl/morpholinomethylpiperidinyl- methyl/pyrrolidinylmethyl-4H-pyran-4-one stru...
journal_title：Bioorganic chemistry
pub_type： 杂志文章
doi：10.1016/j.bioorg.2019.102950
更新日期：2019-07-01 00:00:00
abstract：:Three novel series of triazolophthalazine derivatives bearing hydrazone moiety were designed, synthesized, and evaluated for their anticancer activity against four human cancer cell lines by MTT assay. Six derivatives demonstrated comparable activity with Doxorubicin reference drug against the selected cancer cells. E...
journal_title：Bioorganic chemistry
pub_type： 杂志文章
doi：10.1016/j.bioorg.2020.103899
更新日期：2020-07-01 00:00:00
abstract：:Natural antioxidants and vitamins have potential to protect biological systems from peroxidative damage induced by peroxyl radicals, α-tocopherol (Vitamin E, lipid soluble) and ascorbic acid (vitamin C, water soluble), well known natural antioxidant molecules. In the present study we described the synthesis and biolog...
journal_title：Bioorganic chemistry
pub_type： 杂志文章
doi：10.1016/j.bioorg.2018.02.025
更新日期：2019-02-01 00:00:00
abstract：:8-Chrysoeriol, a bioactive flavanoid, was firstly identified to bind directly to BCL-2 as BH3 mimetics by structure-based virtual ligand screening. And 3D docking model revealed the molecular basis of 8-Chrysoeriol targeting to BCL-2. The interaction between 8-Chrysoeriol and BCL-2 was further confirmed using Microsca...
journal_title：Bioorganic chemistry
pub_type： 杂志文章
doi：10.1016/j.bioorg.2018.01.042
更新日期：2018-04-01 00:00:00
abstract：:In efforts to develop new antitubercular agents, we report here the synthesis of a series of novel pyrrole hydrazine derivatives. The molecules were evaluated against inhibitors of InhA, which is one of the key enzymes involved in type II fatty acid biosynthetic pathway of the mycobacterial cell wall as well as inhibi...
journal_title：Bioorganic chemistry
pub_type： 杂志文章
doi：10.1016/j.bioorg.2017.09.008
更新日期：2017-12-01 00:00:00
