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Bioorganic Chemistry

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https://www.readbyqxmd.com/read/29783098/design-and-synthesis-of-aminocoumarin-derivatives-as-dpp-iv-inhibitors-and-anticancer-agents
#1
Rina Soni, Shubhangi S Soman
DPP-IV "a moonlighting protein" has immerged as promising pathway to control Type 2 diabetes as well as found to play key role in earlier stages of cancer. Here we have reported design, synthesis and applications of aminocoumarin derivatives as DPP-IV inhibitors. Compounds have been synthesized and studied for their DPP-IV inhibition activity. Three compounds have shown moderate inhibition at 100 µM concentration. All compounds were also screened for their anticancer activity against A549 (Lung cancer cell line), MCF-7 (Breast cancer cell line) using MTT assay...
May 17, 2018: Bioorganic Chemistry
https://www.readbyqxmd.com/read/29778797/discovery-of-potent-%C3%AE-glucosidase-inhibitor-flavonols-insights-into-mechanism-of-action-through-inhibition-kinetics-and-docking-simulations
#2
Didem Şöhretoğlu, Suat Sari, Burak Barut, Arzu Özel
Beside other pharmaceutical benefits, flavonoids are known for their potent α-glucosidase inhibition. In the present study, we investigated α-glucosidase inhibitory effects of structurally related 11 flavonols, among which quercetin-3-O-(3″-O-galloyl)-β-galactopyranoside (8) and quercetin 3-O-(6″-O-galloyl)-β-glucopyranoside (9) showed significant inhibition compared to the positive control, acarbose, with IC50 values of 0.97 ± 0.02 and 1.35 ± 0.06 µM, respectively. It was found that while sugar substitution to C3-OH of C ring reduced the α-glucosidase inhibitory effect, galloyl substitution to these sugar units increased it...
May 17, 2018: Bioorganic Chemistry
https://www.readbyqxmd.com/read/29775950/drechmerin-h-a-novel-1-2-2-18-diseco-indole-diterpenoid-from-the-fungus-drechmeria-sp-as-a-natural-agonist-of-human-pregnane-x-receptor
#3
Jian-Chao Zhao, Zhi-Lin Luan, Jia-Hao Liang, Zhong-Bin Cheng, Cheng-Peng Sun, Ya-Li Wang, Meng-Yue Zhang, Tian-Yuan Zhang, Yong Wang, Tian-Mei Yang, Ying-Ying Wu, Yi-Xuan Zhang, Xin-Yu Zhao, Xiao-Chi Ma
A novel 1(2), 2(18)-diseco indole diterpenoid, drechmerin H (1), was isolated from the fermentation broth of Drechmeria sp. together with a new indole diterpenoid, 2'-epi terpendole A (3), and a known analogue, terpendole A (2). Their structures were determined by HRESIMS, 1D and 2D NMR, ECD, and X-ray single crystal diffraction analyses as well as quantum chemical calculation. The abosulte configuration of terpendole A (2) was determined for the first time. Compound 1 displayed the significant agonistic effect on pregnane X receptor (PXR) with EC50 value of 134...
May 9, 2018: Bioorganic Chemistry
https://www.readbyqxmd.com/read/29775947/hit-optimization-studies-of-3-hydroxy-indolin-2-one-analogs-as-potential-anti-hiv-1-agents
#4
Subhash Chander, Cheng-Run Tang, Ashok Penta, Ping Wang, Deepak P Bhagwat, Nicolas Vanthuyne, Muriel Albalat, Payal Patel, Sanskruti Sankpal, Yong-Tang Zheng, Murugesan Sankaranarayanan
In the current study, twenty-two compounds based upon 3-hydroxy-3-(2-oxo-2-phenylethyl)indolin-2-one nucleus were designed, synthesized and in vitro evaluated for HIV-1 RT inhibition and anti-HIV-1 activity. Compounds 3d, 5c and 5e demonstrated encouraging potency against RT enzyme as well as HIV-1 in low micromolar to nanomolar concentration with good to excellent safety index. Structure activity relationship studies revealed that halogens such as bromo or chloro at 5th the position of oxindole ring remarkably enhanced the potency against RT...
May 9, 2018: Bioorganic Chemistry
https://www.readbyqxmd.com/read/29778798/discovery-of-antitumor-ursolic-acid-long-chain-diamine-derivatives-as-potent-inhibitors-of-nf-%C3%AE%C2%BAb
#5
Wei Jiang, Ri-Zhen Huang, Jing Zhang, Tong Guo, Meng-Ting Zhang, Xiao-Chao Huang, Bin Zhang, Zhi-Xin Liao, Jing Sun, Heng-Shan Wang
A series of inhibitors of NF-κB based on ursolic acid (UA) derivatives containing long-chain diamine moieties were designed and synthesized as well as evaluated the antitumor effects. These compounds exhibited significant inhibitory activity to the NF-κB with IC50 values at micromolar concentrations in A549 lung cancer cell line. Among them, compound 8c exerted potent activity against the test tumor cell lines including multidrug resistant human cancer lines, with the IC50 values ranged from 5.22 to 8.95 μM...
May 8, 2018: Bioorganic Chemistry
https://www.readbyqxmd.com/read/29775949/design-and-synthesis-of-some-new-carboxamide-and-propanamide-derivatives-bearing-phenylpyridazine-as-a-core-ring-and-the-investigation-of-their-inhibitory-potential-on-in-vitro-acetylcholinesterase-and-butyrylcholinesterase
#6
Burcu Kilic, Hayrettin O Gulcan, Fatma Aksakal, Tugba Ercetin, Nihan Oruklu, E Umit Bagriacik, Deniz S Dogruer
A series of new carboxamide and propanamide derivatives bearing phenylpyridazine as a core ring were designed, synthesized and evaluated for their ability to inhibit both cholinesterase enzymes. In addition, a series of carboxamide and propanamide derivatives bearing biphenyl instead of phenylpyridazine were also synthesized to examine the inhibitory effect of pyridazine moiety on both cholinesterase enzymes. The inhibitory activity results revealed that compounds 5b, 5f, 5h, 5j, 5l pyridazine-3-carboxamide derivative, exhibited selective acetylcholinesterase (AChE) inhibition with IC50 values ranging from 0...
May 8, 2018: Bioorganic Chemistry
https://www.readbyqxmd.com/read/29763804/chalcones-and-bis-chalcones-as-potential-%C3%AE-amylase-inhibitors-synthesis-in-vitro-screening-and-molecular-modelling-studies
#7
Adebayo Tajudeen Bale, Khalid Mohammed Khan, Uzma Salar, Sridevi Chigurupati, Tolulope Fasina, Farman Ali, Kanwal, Abdul Wadood, Muhammad Taha, Sitanshu Sekhar Nanda, Mehreen Ghufran, Shahnaz Perveen
Despite of a diverse range of biological activities associated with chalcones and bis-chalcones, they are still neglected by the medicinal chemist for their possible α-amylase inhibitory activity. So, the current study is based on the evaluation of this class for the identification of new leads as α-amylase inhibitors. For that purpose, a library of substituted chalcones 1-13 and bis-chalcones 14-18 were synthesized and characterized by spectroscopic techniques EI-MS and 1 H NMR. CHN analysis was carried out and found in agreement with the calculated values...
May 7, 2018: Bioorganic Chemistry
https://www.readbyqxmd.com/read/29758407/synthesis-and-molecular-docking-of-n-n-disubstituted-thiourea-derivatives-as-novel-aromatase-inhibitors
#8
Ratchanok Pingaew, Veda Prachayasittikul, Nuttapat Anuwongcharoen, Supaluk Prachayasittikul, Somsak Ruchirawat, Virapong Prachayasittikul
A three series of thioureas, monothiourea type I (4a-g), 1,4-bisthiourea type II (5a-h) and 1,3-bisthiourea type III (6a-h) were synthesized. Their aromatase inhibitory activities have been evaluated. Interestingly, eight thiourea derivatives (4e, 5f-h, 6d, 6f-h) exhibited the aromatase inhibitory activities with IC50 range of 0.6-10.2 μM. The meta-bisthiourea bearing 4-NO2 group (6f) and 3,5-diCF3 groups (6h) were shown to be the most potent compounds with sub-micromolar IC50 values of 0.8 and 0.6 μM, respectively...
May 4, 2018: Bioorganic Chemistry
https://www.readbyqxmd.com/read/29775948/novel-3-phenylcoumarin-lipoic-acid-conjugates-as-multi-functional-agents-for-potential-treatment-of-alzheimer-s-disease
#9
Leili Jalili-Baleh, Hamid Nadri, Hamid Forootanfar, Alireza Samzadeh-Kermani, Tuba Tüylü Küçükkılınç, Beyza Ayazgok, Mahban Rahimifard, Maryam Baeeri, Mohsen Doostmohammadi, Loghman Firoozpour, Syed Nasir Abbas Bukhari, Mohammad Abdollahi, Mohammad Reza Ganjali, Saeed Emami, Mehdi Khoobi, Alireza Foroumadi
New series of triazole-containing 3-phenylcoumarin-lipoic acid conjugates were designed as multi-functional agents for treatment of Alzheimer's disease. The target compounds 4a-o were synthesized via the azide-alkyne cycloaddition reaction and their biological activities were primarily evaluated in terms of neuroprotection against H2 O2 -induced cell death in PC12 cells and AChE/BuChE inhibition. The promising compounds 4j and 4i containing four carbons spacer were selected for further biological evaluations...
May 2, 2018: Bioorganic Chemistry
https://www.readbyqxmd.com/read/29772469/synthesis-of-steroidal-imidazolidinthiones-as-potential-apoptotic-agents-investigation-by-theoretical-and-experimental-studies
#10
Ayaz Mahmood Dar, Rizwan Nabi, Shafia Mir, Manzoor Ahmad Gatoo, Shamsuzzaman, Shabir H Lone
New steroidal imidazolidinthione derivatives (4-6) were synthesized from steroidal thiosemicarbazones and dichloroethane. The synthesized compounds were characterized using spectral data analysis. Theoretical DFT involving B3LYP/6-31G∗∗ level of theory was employed to gain insights into the molecular structure of the target compounds. MEPS and FMO analysis were carried out. HOMO-LUMO energy gap was determined which helped to evaluate various global descriptors like hardness, chemical potential, electronegativity, nucleophilicity and electrophilicity index, etc...
May 2, 2018: Bioorganic Chemistry
https://www.readbyqxmd.com/read/29751319/molecular-modelling-and-synthesis-of-spiroimidazolidine-2-4-diones-with-dual-activities-as-hypoglycemic-agents-and-selective-inhibitors-of-aldose-reductase
#11
Manar G Salem, Yasmine M Abdel Aziz, Marwa Elewa, Hosam A Elshihawy, Mohamed M Said
Novel derivatives of spiroimidazolidinedione were synthesized and evaluated as hypoglycemic agents through binding to sulfonylurea receptor 1 (SUR1) in pancreatic beta-cells. Their selectivity index was calculated against both aldehyde reductase (ALR1) and aldose reductase (ALR2). Aldehyde reductase is a key enzyme in the polyol pathway that is involved in the etiology of the secondary diabetic complications. All structures were confirmed by microanalysis and by IR, 1 H NMR, 13 C NMR and EI-MS spectroscopy...
May 2, 2018: Bioorganic Chemistry
https://www.readbyqxmd.com/read/29772470/synthesis-molecular-docking-and-xanthine-oxidase-inhibitory-activity-of-5-aryl-1h-tetrazoles
#12
Itrat Fatima, Humaira Zafar, Khalid Mohammed Khan, Syed Muhammad Saad, Sumaira Javaid, Shahnaz Perveen, M Iqbal Choudhary
5-Aryl-1H-tetrazoles (1-24) were synthesized and screened for their xanthine oxidase (XO) inhibitory activity using allopurinol as standard inhibitor (IC50  = 2.0 ± 0.01 µM). Six compounds 3, 4, 5, 9, 21, and 24 exhibited significant to weak activities with IC50 values in the range of 7.4-174.2 µM. Active compounds were further subjected to kinetic and molecular docking studies to deduce their modes of inhibition, and to study their interactions with the protein (XO) at atomic level, respectively...
May 1, 2018: Bioorganic Chemistry
https://www.readbyqxmd.com/read/29751320/structure-activity-relationships-of-rationally-designed-amacr-1a-inhibitors
#13
Maksims Yevglevskis, Guat L Lee, Amit Nathubhai, Yoana D Petrova, Tony D James, Michael D Threadgill, Timothy J Woodman, Matthew D Lloyd
α-Methylacyl-CoA racemase (AMACR; P504S) is a promising novel drug target for prostate and other cancers. Assaying enzyme activity is difficult due to the reversibility of the 'racemisation' reaction and the difficulties in the separation of epimeric products; consequently few inhibitors have been described and no structure-activity relationship study has been performed. This paper describes the first structure-activity relationship study, in which a series of 23 known and potential rational AMACR inhibitors were evaluated...
April 30, 2018: Bioorganic Chemistry
https://www.readbyqxmd.com/read/29738972/steroids-from-ganoderma-sinense-as-new-natural-inhibitors-of-cancer-associated-mutant-idh1
#14
Mengzhu Zheng, Ruotian Tang, Yue Deng, Kaiyin Yang, Lixia Chen, Hua Li
Isocitrate dehydrogenase (IDH) is one of the key enzymes in the tricarboxylic acid cycle, and IDH mutations have been associated with many cancers, including glioblastoma, sarcoma, acute myeloid leukemia, etc. Three natural steroids 1-3 from Ganoderma sinense, a unique and rare edible-medicinal fungi in China, were found as potential IDH1 inhibitors by virtual ligand screening method. Among the three compounds, 3 showed the highest binding affinity to IDH1 with significant calculated binding free energy. Enzymatic kinetics demonstrated that 3 inhibited mutant enzyme in a noncompetitive manner...
April 30, 2018: Bioorganic Chemistry
https://www.readbyqxmd.com/read/29738970/a-novel-derivatives-of-thiazol-4-5h-one-and-their-activity-in-the-inhibition-of-11%C3%AE-hydroxysteroid-dehydrogenase-type-1
#15
Renata Studzińska, Renata Kołodziejska, Daria Kupczyk, Wojciech Płaziński, Tomasz Kosmalski
11β-Hydroxysteroid dehydrogenase type 1 (11β-HSD1) is an enzyme that catalyzes the conversion of inactive cortisone into physiologically active cortisol. Inhibiting the activity of this enzyme plays a key role in the treatment of Cushing's syndrome, metabolic syndrome and type 2 diabetes. Therefore, new compounds that are selective inhibitors of this enzyme are constantly being looked for. In this work we present the synthesis of 2-(allylamino)thiazol-4(5H)-one derivatives by the reaction of N-allylthiourea with appropriate α-bromoesters...
April 30, 2018: Bioorganic Chemistry
https://www.readbyqxmd.com/read/29738969/novel-tetrahydrofuran-derivatives-from-trigonostemon-howii-with-their-potential-anti-hiv-1-activities
#16
Yan-Ping Liu, Wan-Hui Zhao, Xing-Yang Feng, Zhi-Jie Zhang, Kang Zong, Zhi-Guo Sun, Yong-Tang Zheng, Yan-Hui Fu
A novel tetrahydrofuran derivative, trigonohowine (1), together with five known tetrahydrofuran derivatives (2-6), were isolated from the stems and leaves of Trigonostemon howii. The structure of 1 was elucidated by extensive spectroscopic methods and the known compounds were identified by comparisons with the data reported in literature. Among them, trigonohowine (1) represents the first example of a new type of tetrahydrofuran derivative, possessing an unprecedented carbon skeleton containing 23 carbon atoms on the carbon skeleton and the known compouds (2-6) are rare tetrahydrofuran derivatives in the plant kingdom with various carbon skeletons...
April 30, 2018: Bioorganic Chemistry
https://www.readbyqxmd.com/read/29738968/novel-%C3%AE-lactone-derivatives-from-trigonostemon-heterophyllus-with-their-potential-antiproliferative-activities
#17
Yan-Ping Liu, Shi Hu, Qing Wen, Yan-Lei Ma, Zhi-Hua Jiang, Jin-Ying Tang, Yan-Hui Fu
Two novel γ-lactone derivatives, trigoheterophines A (1) and B (2), together with four known furan derivatives (3-6), were isolated from the stems and leaves of Trigonostemon heterophyllus. The structures of 1 and 2 were elucidated by extensive spectroscopic methods and the known compounds were identified by comparing with the data reported in literature. Among them, trigoheterophines A (1) and B (2) represent an unusual type of γ-lactone derivatives, possessing 21 carbon atoms on the carbon skeleton, and known compouds (3-6) are rare furan derivatives in the plant kingdom with diverse long-chain hydrocarbyl groups as substituents at C-4...
April 30, 2018: Bioorganic Chemistry
https://www.readbyqxmd.com/read/29783099/leveraging-the-cruzain-s3-subsite-to-increase-affinity-for-reversible-covalent-inhibitors
#18
Lorenzo Cianni, Geraldo Sartori, Fabiana Rosini, Daniela De Vita, Gabriel Pires, Bianca Rebelo Lopes, Andrei Leitão, Antonio C B Burtoloso, Carlos A Montanari
Cruzain is the major cysteine protease of Trypanosoma cruzi, the etiological agent of Chagas disease. Reversible covalent cruzain inhibitors can block the steps of cell differentiation in the parasite and kill the organism. To this end, the description of how inhibitors modified at the P2/P3 positions lead to analogs with greater cruzain affinity to the S2/S3 subsites is of fundamental importance. Albeit many efforts are being employed in the characterization of the interaction processes with S2 subsite, little is known about the cruzain S3 subsite...
April 26, 2018: Bioorganic Chemistry
https://www.readbyqxmd.com/read/29751321/synthesis-biological-evaluation-and-molecular-modeling-of-2-amino-2-phenylethanol-derivatives-as-novel-%C3%AE-2-adrenoceptor-agonists
#19
Xinyue Ge, Yongmei Mo, Gang Xing, Lei Ji, Haiyan Zhao, Jianfang Chen, Bin He, Xuyao Chen, Ruijuan Xing, Xiaoqiang Li, Ying Zhao, Jinyan Li, Haining Yan, Anthony Yiu-Ho Woo, Yuyang Zhang, Bin Lin, Li Pan, Maosheng Cheng
A novel series of 2-amino-2-phenylethanol derivatives were developed as β2 -adrenoceptor agonists. Among them, 2-amino-3-fluoro-5-(2-hydroxy-1-(isopropylamino)ethyl)benzonitrile (compound 2f) exhibited the highest activity (EC50 = 0.25 nM) in stimulating β2 -adrenoceptor-mediated cellular cAMP production with a 763.6-fold selectivity over the β1 -adrenoceptor. The (S)-isomer of 2f was subsequently found to be 8.5-fold more active than the (R)-isomer. Molecular docking was performed to determine the putative binding modes of this new class of β2 -adrenoceptor agonists...
April 26, 2018: Bioorganic Chemistry
https://www.readbyqxmd.com/read/29738971/sophoflavanones-a-and-b-two-novel-prenylated-flavanones-from-the-roots-of-sophora-flavescens
#20
Hui Zhu, Ya-Nan Yang, Zi-Ming Feng, Jian-Shuang Jiang, Pei-Cheng Zhang
In our ongoing investigation of the bioactive compounds from the extract of the roots of Sophora flavescens, two novel prenylated flavanones, named sophoflavanones A (1) and B (2), each with an unusual pyran ring were isolated. Their structures, as well as their absolute configurations, were elucidated based on spectroscopic data including a comparison of their experimental and calculated electronic circular dichroism (ECD) spectra. Additionally, compounds 1 and 2 showed moderate antioxidant activities against Fe2+ /cysteine-induced toxicity at a concentration of 0...
April 26, 2018: Bioorganic Chemistry
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