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Bioorganic Chemistry

Mohamed A Abdelgawad, Madlen B Labib, Waleed A M Ali, Gehan Kamel, Amany A Azouz, El-Shaymaa El-Nahass
A series of newly synthesized 4-aryl-hydrazonopyrazolones were designed and their structures were confirmed by spectral and elemental analyses. All synthesized compounds were evaluated for their in vitro COXs, 5-LOX inhibition, in vivo analgesic and anti-inflammatory activities. Compounds 5d, 5f and 5i were found to be the most potent COX-2/5-LOX inhibitors with superior COX-2 selectivity index values (SI = 5.29-5.69) to reference standard celecoxib (SI = 3.52). Four compounds; 5b, 5c, 5d and 5f showed excellent anti-inflammatory activity (% edema inhibition = 72...
March 8, 2018: Bioorganic Chemistry
Boddu Rama Krishna, Dinesh Thummuri, V G M Naidu, Sistla Ramakrishna, Uppuluri Venkata Mallavadhani
A total of twenty-two novel coumarin triazole hybrids (4a-4k and 6a-6k) were synthesized from orcinol in good to excellent yields of 70-94%. The structures of all the synthesized compounds were elucidated by spectroscopic techniques such as1 H NMR,13 C NMR, and HRMS. The anti-inflammatory potential of synthesized compounds was investigated against the proinflammatory cytokine, TNF-α on U937 cell line and compounds 4d, 4j, and 6j were found to exhibit promising anti-inflammatory activity. These three compounds were further screened against TNF-α on LPS-stimulated RAW 264...
March 7, 2018: Bioorganic Chemistry
Leila Dehestani, Nematollah Ahangar, Seyedeh Mahdieh Hashemi, Hamid Irannejad, Patrick Honarchian Masihi, Aidin Shakiba, Saeed Emami
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 MES and PTZ tests revealed that they are more effective in MES model respect to PTZ test. All compounds showed 33-100% protection against MES-induced seizures at the dose of 100 mg/kg...
March 7, 2018: Bioorganic Chemistry
Sylvie Daunes, Claudius D'Silva
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 derivatives containing ethyl side chains showed lower in vitro activity than those with methyl side chains 1-4, IC50  ∼ 5...
March 7, 2018: Bioorganic Chemistry
Hayat Ullah, Fazal Rahim, Muhammad Taha, Imad Uddin, Abdul Wadood, Syed Adnan Ali Shah, Rai Khalid Farooq, Mohsan Nawaz, Zainul Wahab, Khalid Mohammed Khan
We have synthesized oxadiazole derivatives (1-16), characterized by1 H NMR,13 C NMR and HREI-MS and screened for thymidine phosphorylase inhibitory potential. All derivatives display varied degree of thymidine phosphorylase inhibition in the range of 1.10 ± 0.05 to 49.60 ± 1.30 μM when compared with the standard inhibitor 7-Deazaxanthine having an IC50 value 38.68 ± 1.12 μM. Structure activity relationships (SAR) has been established for all compounds to explore the role of substitution and nature of functional group attached to the phenyl ring which applies imperious effect on thymidine phosphorylase activity...
March 7, 2018: Bioorganic Chemistry
Gamal Badr, Halise Inci Gul, Cem Yamali, Amal A M Mohamed, Badr M Badr, Mustafa Gul, Ahmad Abo Markeb, Nagwa Abo El-Maali
Recent developments in the literature have demonstrated that curcumin exhibit antioxidant properties supporting its anti-inflammatory, chemopreventive and antitumoral activities against aggressive and recurrent cancers. Despite the valuable findings of curcumin against different cancer cells, the clinical use of curcumin in cancer treatment is limited due to its extremely low aqueous solubility and instability, which lead to poor in vivo bioavailability and limited therapeutic effects. We therefore focused in the present study to evaluate the anti-tumor potential of curcumin analogues on the human breast carcinoma cell lines MDA-MB-231 and MCF-7, as well as their effects on non-tumorigenic normal breast epithelial cells (MCF-10)...
March 7, 2018: Bioorganic Chemistry
Zuo Peng Li, Hyeong-Hwan Lee, Zia Uddin, Yeong Hun Song, Ki Hun Park
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 evaluated against protein tyrosine phosphatase 1B (PTP1B), which plays an important role in diabetes, obesity, and cancer...
March 7, 2018: Bioorganic Chemistry
Mohamed K S El-Nagar, Hajjaj H M Abdu-Allah, Ola I A Salem, Abdel-Hamid N Kafafy, Hanan S M Farghaly
Three new series of 5-aminosalicylic acid derivatives; series I (14, 16-18), series II (19-30) and series III (31-41) were synthesized as potential dual COX-2/5-LOX inhibitors. Their chemical structures were confirmed using spectroscopic tools including IR,1 H NMR,13 C NMR, mass spectroscopy and elemental analyses. The anti-inflammatory activity for all target compounds was evaluated in vivo using carrageenan-induced paw edema. Compound 36 showed the highest anti-inflammatory activity (114.12%) relative to reference drug indomethacin at 4 h interval...
March 6, 2018: Bioorganic Chemistry
Marek Bajda, Kamil Łątka, Michalina Hebda, Jakub Jończyk, Barbara Malawska
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 16 (3-(4-phenyl-piperazin-1-ylmethyl)-phenyl phenylcarbamate) turned out to be the most active (IC50  = 2...
March 3, 2018: Bioorganic Chemistry
Haitham Elleuch, Wafa Mihoubi, Mohamed Mihoubi, Emna Ketata, Ali Gargouri, Farhat Rezgui
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) scavenging activities of MBH alcohols and their derivatives including acetates, phosphonates and hydrazonophosphonates...
March 3, 2018: Bioorganic Chemistry
Muhammad Taha, Syed Adnan Ali Shah, Muhammad Afifi, Syahrul Imran, Sadia Sultan, Fazal Rahim, Nor Hadiani Ismail, Khalid Mohammed Khan
Thymidine phosphorylase (TP) over expression plays role in several pathological conditions, such as rheumatoid arthritis, chronic inflammatory diseases, psoriasis, and tumor angiogenesis. The inhibitor of this enzyme plays an important role in preventing the serious threat due to over expression of TP. In this regard, a series of seventeenanalogs of 3-formylcoumarin (1-17) were synthesized, characterized by1 HNMR and EI-MS and screened for thymidine phosphorylaseinhibitory activity. All analogs showed a variable degree of thymidine phosphorylase inhibition with IC50 values ranging between 0...
March 1, 2018: Bioorganic Chemistry
Murat Bozdag, Fabrizio Carta, Andrea Angeli, Sameh M Osman, Fatmah A S Alasmary, Zeid AlOthman, Claudiu T Supuran
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, 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 the widespread cytosolic isoforms hCA I and II, but they inhibited the tumor associated isoforms with interesting potencies...
March 1, 2018: Bioorganic Chemistry
Bhupinder Kumar, Praveen Sharma, Vivek Prakash Gupta, Madhu Khullar, Sandeep Singh, Nilambra Dogra, Vinod Kumar
A number of pyrimidine bridged combretastatin derivatives were designed, synthesized and evaluated for anticancer activities against breast cancer (MCF-7) and lung cancer (A549) cell lines using MTT assays. Most of the synthesized compounds displayed good anticancer activity with IC50 values in low micro-molar range. Compounds 4a and 4p were found most potent in the series with IC50 values of 4.67 µM & 3.38 µM and 4.63 µM & 3.71 µM against MCF7 and A549 cancer cell lines, respectively. Biological evaluation of these compounds showed that selective cancer cell toxicity (in vitro using human lung and breast cancer cell lines) might be due to the inhibition of antioxidant enzymes instigating elevated ROS levels which triggers intrinsic apoptotic pathways...
February 28, 2018: Bioorganic Chemistry
Adejoke N Kolawole, Valentine T Akinladejo, Olusola O Elekofehinti, Afolabi C Akinmoladun, Ayodele O Kolawole
Aldehyde dehydrogenases (ALDHs) are a diverse family of enzymes that catalyze the NAD(P)+ -dependent detoxification of toxic aldehyde compounds. ALDHs are also involved in non-enzymatic ligand binding to endobiotics and xenobiotics. Here, the enzyme crucial non-canonical and non-catalytic interaction with kolaflavanone, a component of kolaviron, and a major bioflavonoid isolated from Garcinia kola (Bitter kola) was characterized by various spectroscopic and in silico approaches under stimulated physiological condition...
February 27, 2018: Bioorganic Chemistry
Hanmanth Reddy Vulupala, Yasodakrishna Sajja, Pankaj K Bagul, Raviteja Bandla, Lingaiah Nagarapu, Sanjay K Benerjee
A novel triazole derivatives(±)-2-(hydroxymethyl)-7,8-dihydro-1H-indeno[5,4-b]furan-6(2H)-one (12a-j) were designed and synthesized by the reaction between racemic azide and terminal acetylenes under click chemistry reaction conditions followed by biological evaluation as angiotensin converting enzyme (ACE) inhibitors. β-Amino alcohol derivatives of 1-indanone (15a-l) were synthesized from 5-hydroxy indanone, it was reacted with epichlorohydrin and followed by oxirane ring opening with various piperazine derivatives...
February 24, 2018: Bioorganic Chemistry
Maryam Naseri, Seyyed Ahmad Emami, Javad Asili, Zahra Tayarani-Najaran, Gholamreza Dehghan, Bernd Schneider, Mehrdad Iranshahi
Phytochemical investigation of the dichloromethane extract of the dried aerial parts of Corydalis rupestris (Papaveraceae) resulted in the identification of four new isoquinoline alkaloids rupestrines A-D and one known isoquinoline alkaloid, namely, stylopine. The structures of these compounds were characterized by extensive spectroscopic methods including 1D- (1 H and13 C) and 2D NMR experiments (COSY, HSQC, HMBC, and NOESY) as well as HRESIMS analyses. In addition, the absolute configurations of rupestrines A-D were determined using modified Mosher's method...
February 24, 2018: Bioorganic Chemistry
Alessio Nocentini, Davide Moi, Gianfranco Balboni, Severo Salvadori, Valentina Onnis, Claudiu T Supuran
Herein we report the synthesis of a new series of aromatic sulfamates designed considering the sulfonamide COX-2 selective inhibitors celecoxib and valdecoxib as lead compounds. These latter were shown to possess important human carbonic anhydrase (CA, EC inhibitory properties, with the inhibition of the tumor-associated isoform hCA IX likely being co-responsible of the celecoxib anti-tumor effects. Bioisosteric substitution of the pyrazole or isoxazole rings from these drugs with the pyrazoline one was considered owing to the multiple biological activities ascribed to this latter heterocycle and paired with the replacement of the sulfonamide of celecoxib and valdecoxib with its equally potent bioisoster sulfamate...
February 23, 2018: Bioorganic Chemistry
Thao Quyen Cao, Quynh-Mai Thi Ngo, Su Hui Seong, Ui Joung Youn, Jeong Ah Kim, Junheon Kim, Jin-Cheol Kim, Mi Hee Woo, Jae Sue Choi, Byung Sun Min
Coptis chinensis has been used as a medicinal herb in traditional oriental medicine. In this study, chemical investigation of a water extract of C. chinensis identified two new quaternary protoberberines (1, 2), a new tricyclic amide (3), together with five known compounds. Their chemical structures were elucidated by analysis with 1D and 2D NMR and high-resolution mass spectroscopy, as well as by comparison with those reported in the literature. Compounds 4, 5, and 7 showed potent inhibition against acetylcholinesterase (AChE) with IC50 values of 1...
February 23, 2018: Bioorganic Chemistry
Muhammad Taha, Syed Adnan Ali Shah, Muhammad Afifi, Syahrul Imran, Sadia Sultan, Fazal Rahim, Khalid Mohammed Khan
We have synthesized seventeen Coumarin based derivatives (1-17), characterized by1 HNMR,13 CNMR and EI-MS and evaluated for α-glucosidase inhibitory potential. Among the series, all derivatives exhibited outstanding α-glucosidase inhibition with IC50 values ranging between 1.10 ± 0.01 and 36.46 ± 0.70 μM when compared with the standard inhibitor acarbose having IC50 value 39.45 ± 0.10 μM. The most potent derivative among the series is derivative 3 having IC50 value 1.10 ± 0.01 μM, which are many folds better than the standard acarbose...
February 17, 2018: Bioorganic Chemistry
Jiayue Xi, Siyuan Xu, Lulu Zhang, Xueyuan Bi, Yanshen Ren, Yu-Chih Liu, Yueqing Gu, Yungen Xu, Fei Lan, Xiaoming Zha
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 LSD1 in vitro (IC50  = 4 μM). Molecular docking was conducted to predict its binding mode. Furthermore, 10d displayed it could inhibit migration of HCT-116 colon cancer cells and A549 lung cancer cells...
February 16, 2018: Bioorganic Chemistry
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