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Bioorganic Chemistry

Paweł Borowiecki, Maciej Dranka
Compounds possessing propargylic (prop-2-ynylic) system are very important building blocks for organic chemistry. Among them, preparation of enantiomeric homopropargyl alcohols (but-3-yn-1-ols) constitutes a key-challenge for asymmetric synthesis and thus drawn tremendous attention from the synthetic community in the last few decades. In this work, the catalytic performance of a set of commercial lipases has been investigated for enantioselective transesterification of 1-phenylhomopropargylic alcohols under kinetically-controlled conditions...
February 11, 2019: Bioorganic Chemistry
Marta Domżał-Kędzia, Agnieszka Lewińska, Anna Jaromin, Marek Weselski, Robert Pluskota, Marcin Łukaszewicz
Levan is a polysaccharide composed of fructose units with β-2,6-glycoside bonds. Microorganisms synthesize levan by levansucrase as a mixture of low- and high-molecular-weight fractions. Due to its properties, it has a wide range of applications in cosmetics, pharmaceuticals, food and medicine; it appears that the molecular weight of levan might impact its industrial use. To obtain one fraction of levan after biotransformation, ethanol precipitation with an increasing volume of alcohol was conducted. This precipitation process was also optimized...
February 11, 2019: Bioorganic Chemistry
P Thangarasu, A Manikandan, S Thamaraiselvi
As the global need for drugs getting increases, the necessity of novel and effective drugs are the need of the day. Pyrazoles are one of the active molecules in novel drug discovery. The present study deals about the synthesis of precursors 4-(4-fluorophenyl)-6-isopropyl-2-(methylsulfonyl) pyrimidine-5-carbohydrazides (3a-m) from methyl-4-(4-fluorophenyl)-6-isopropyl-2-(methyl sulfonyl) pyrimidine-5-carboxylate (2) by treating with substituted acetophenone. Further, Vilsmeier-Haack reaction of compounds 3a-m at 70 °C for 8-10 hrs gave novel pyrazole carbaldehyde derivatives (4a-m) in good yield...
February 7, 2019: Bioorganic Chemistry
Sandra Sordon, Jarosław Popłoński, Tomasz Tronina, Ewa Huszcza
In the present study, the species: Beauveria bassiana, Absidia coerulea and Absidia glauca were used in biotransformation of flavones (chrysin, apigenin, luteolin, diosmetin) and flavanones (pinocembrin, naringenin, eriodictyol, hesperetin). The Beauveria bassiana AM 278 strain catalyzed the methylglucose attachment reactions to the flavonoid molecule at positions C7 and C3'. The application of the Absidia genus (A. coerulea AM 93, A. glauca AM 177) as the biocatalyst resulted in the formation of glucosides with a sugar molecule present at C7 and C3' positions of flavonoids skeleton...
February 7, 2019: Bioorganic Chemistry
Fikret Turkan, Adnan Cetin, Parham Taslimi, Muhammet Karaman, İlhami Gulçin
A series of substituted pyrazole compounds (1-8 and 9a, b) were synthesized and their structure was characterized by IR, NMR, and Mass analysis. These obtained novel pyrazole derivatives (1-8 and 9a, b) were emerged as effective inhibitors of the cytosolic carbonic anhydrase I and II isoforms (hCA I and II) and acetylcholinesterase (AChE) enzymes with Ki values in the range of 1.03 ± 0.23-22.65 ± 5.36 µM for hCA I, 1.82 ± 0.30-27.94 ± 4.74 µM for hCA II, and 48.94 ± 9.63-116.05 ± 14...
February 5, 2019: Bioorganic Chemistry
Noor Atatreh, Amal M Youssef, Mohammad A Ghattas, Mohammad Al Sorkhy, Sara Alrawashdeh, Khaled B Al-Harbi, Ibrahim M El-Ashmawy, Tariq I Almundarij, Amani A Abdelghani, Alaa S Abd-El-Aziz
In this study, the acid chlorides of pyrazolo[3,4-d]pyrimidine compounds were prepared and reacted with a number of nucleophiles. The novel compounds were experimentally tested via enzyme assay and they showed cyclooxygenase-2 inhibition activity in the middle micro molar range (4b had a COX-1 IC50 of 26 µM and a COX-2 IC50 of 34 µM, 3b had a COX-1 IC50 of 19 µM and a COX-2 IC50 of 31 µM, 3a had a COX-2 IC50 of 42 µM). These compounds were analyzed via docking and were predicted to interact with some of the COX-2 key residues...
February 5, 2019: Bioorganic Chemistry
Pavitra S Thacker, Mallika Alvala, Mohammed Arifuddin, Andrea Angeli, Claudiu T Supuran
A series of novel 7-hydroxycoumarin-3-carboxamides was synthesized by the reaction of 7-hydroxy-2-oxo-2H-chromene-3-carboxylic acid with various substituted aromatic amines. The newly synthesized compounds were evaluated for their inhibitory activity against the four physiologically relevant human carbonic anhydrase (hCA, EC isoforms CA I, CA II, CA IX and CA XII. The CA inhibition results show that the newly synthesized 7-hydroxycoumarin-3-carboxamides (4a-n) exhibited selective inhibition of the tumor associated isoforms, CA IX and CA XII over CA I and II isoforms...
February 5, 2019: Bioorganic Chemistry
Shanchong Chen, Haohua Li, Yuchan Chen, Saini Li, Jianlin Xu, Heng Guo, Zhaoming Liu, Shuang Zhu, Hongxin Liu, Weimin Zhang
Three new diterpenes koninginols A-C (1-3) and two new sesquiterpenoids 11-hydroxy-15-drimeneoic acid (4), koninginol D (5), together with twelve known compounds (6-17) were isolated from the endophytic fungus Trichoderma koningiopsis A729 derived from Morinda officinalis. Their structures were fully assigned with the aid of extensive spectroscopic analysis and reported data from the previous literatures. Koninginols A and B were disclosed as intriguing diterpene alkaloids, whereas the koninginol C was disclosed as one of the two examples of harziandione diterpene...
February 5, 2019: Bioorganic Chemistry
Suat Sari, Burak Barut, Arzu Özel, Ayşe Kuruüzüm-Uz, Didem Şöhretoğlu
Bark of Quercus coccifera is widely used in folk medicine. We tested tyrosinase and α-glucosidase inhibitory effects of Q. coccifera bark extract and isolated compounds from it. The extract inhibited tyrosinase with an IC50 value of 75.13 ± 0.44 µg/mL. Among the isolated compounds, polydatin (6) showed potent tyrosinase inhibition compared to the positive control, kojic acid, with an IC50 value of 4.05 ± 0.30 µg/mL. The Q. coccifera extract also inhibited α-glucosidase significantly with an IC50 value of 3...
February 5, 2019: Bioorganic Chemistry
Kaan Kucukoglu, Halise Inci Gul, Parham Taslimi, Ilhami Gulcin, Claudiu T Supuran
Recently, inhibition of carbonic anhydrase (hCA) and acetylcholinesterase (AChE) have appeared as a promising approach for pharmacological intervention in a variety of disorders such as glaucoma, epilepsy, obesity, cancer, and Alzheimer's disease. Keeping this in mind, N,N'-bis[(1-aryl-3-heteroaryl)propylidene]hydrazine dihydrochlorides, N1-N11, P1, P4-P8, and R1-R6, were synthesized to investigate their inhibitory activity against hCA I, hCA II, and AChE enzymes. All compounds in N, P, and R-series inhibited hCAs (I and II) and AChE more efficiently than the reference compounds acetazolamide (AZA), and tacrine...
February 4, 2019: Bioorganic Chemistry
Ghulam Abbas, Ahmed Al Harrasi, Hidayat Hussain, Ahmed Hamaed, Claudiu T Supuran
Diabetes mellitus is a chronic metabolic disorder which is rapidly spreading worldwide. It is characterized by persistent elevated blood glucose level above normal values (hyperglycemia) due to defect in either insulin secretion or in insulin action or both of them. Currently approved oral synthetic antidiabetic drugs such as biguanides, thiazolidinediones, sulfonylureas, and meglitinides have shown undesirable side effects. Therefore, newer approaches and targets for the management of diabetes mellitus are highly desirable...
February 4, 2019: Bioorganic Chemistry
Mamta, Ranjana Aggarwal, Rachna Sadana, Jeziel Ilag, Garima Sumran
An efficient synthesis of a series of 6-chloro-3-substituted-[1,2,4]triazolo[4,3-b]pyridazines is described via intramolecular oxidative cyclization of various 6-chloropyridazin-3-yl hydrazones with iodobenzene diacetate. The structures of the newly synthesized compounds were assigned on the basis of elemental analysis, IR, NMR (1 H and 13 C) and mass spectral data. All the thirty three compounds 3a-q and 4b-q synthesized in the present study were evaluated for their in vitro cytotoxic activities against two Acute Lymphoblastic Leukemia (ALL) cell lines named, SB-ALL and NALM-6, and a human breast adenocarcinoma cell lines (MCF-7)...
February 2, 2019: Bioorganic Chemistry
Zhen Zeng, Xiaoli Yin, Xueyuan Wang, Wuying Yang, Xiaoqin Liu, Yanping Hong
Twenty maslinic acid and corosolic acid derivatives were obtained by coupling with l-amino acids at C-28 position. The α-glucosidase inhibitory activities of the present compounds were evaluated in vitro. Results reveal that some of the derivatives exhibit a better α-glucosidase inhibitory activity than that of acarbose in the test conditions of ethanol-water solution and DMSO. It is worth noting that maslinic acid and corosolic acid derivatives coupled aspartic acid (9f: IC50  = 382 μm and 10f: IC50  = 364 μm, respectively) have the best water solubility and thus presented higher inhibitory activity than that of acarbose (IC50  = 484 μm)...
February 2, 2019: Bioorganic Chemistry
Bart I Roman
The publication of unfounded health claims on small molecules in peer-reviewed scientific literature is a problem that requires attention. It undermines the evidence-based decision making processes of modern-day society, weakens the credibility of the scientific enterprise, and diverts resources to futile research efforts. In the present essay we discuss some human and scientific causes behind the issue. We propose a number of actions to be taken up by scientists, referees and publishers. One particularly important factor is the issue of enigmatic compound behavior in biological assays...
February 2, 2019: Bioorganic Chemistry
Yahui Ding, Wenwei Pan, Junqing Xu, Tianpeng Wang, Tianyang Chen, Zhongquan Liu, Chunfeng Xie, Quan Zhang
One new eudesmane sesquiterpenoid, 11β-hydroxy-13-chloro-eudesm-5-en-12, 8-olide (1), was isolated from the roots of Inula helenium together with nine eudesmanolides (2-10) and one germacranolide (11). Their structures were elucidated on the basis of detailed spectroscopic analyses. All isolates were evaluated for their antiproliferative activities against human leukemia stem-like cell line KG1a. Compound 10 exhibited the most potent effect with the IC50 value of 3.36 ± 0.18 μM. A further investigation revealed that compound 10 could significantly induce apoptosis of KG1a cells...
January 31, 2019: Bioorganic Chemistry
Abdul-Malek S Al-Tamimi, Mikel Etxebeste-Mitxeltorena, Carmen Sanmartín, Antonio Jiménez-Ruiz, Leo Syrjänen, Seppo Parkkila, Silvia Selleri, Fabrizio Carta, Andrea Angeli, Claudiu T Supuran
We report new organoselenium compounds bearing the sulfonamide moiety as effective inhibitors of the β-isoform of Carbonic Anhydrase from the unicellular parasitic protozoan L. donovani chagasi. All derivatives were evaluated in vitro for their leishmanicidal activities against Leishmania infantum amastigotes along with their cytotoxicities in human THP-1 cells. Compounds 3e-g showed their activity in the low micromolar range with IC50 values spanning from 0.72 to 0.81 µM and selectivity indexes (SI) > 8 (for 3g SI > 30), thus much higher than those observed for the reference drugs miltefosine and edelfosine...
January 31, 2019: Bioorganic Chemistry
Nagat Ghareb, Norhan M El-Sayed, Reda Abdelhameed, Koji Yamada, Mohamed Saleh Elgawish
Targeting of protein tyrosine phosphatase-1B (PTP1B) has emerged as a promising strategy for therapeutic intervention of diabetes and obesity. Investigation of new inhibitors with good bioavailability and high selectivity is the major challenge of drug discovery program targeting PTP1B. Therefore, herein, new neutral benzene-sulfonamide containing compounds were designed, synthesized and biologically evaluated as potent PTP1B inhibitors. New series of thiazolidine, oxazolidine, thiazinan, oxazinan, oxazole, thiazole, tetrazole, cyanopyridine, chromenone, and iminochromene of benzene-sulfonamide derivatives (MSE-1 to MSE-15) were synthesized in a good yield under mild condition using sulfadiazine as a starting material...
January 31, 2019: Bioorganic Chemistry
Silvia Gobbi, Qingzhong Hu, Giacomo Foschi, Elena Catanzaro, Federica Belluti, Angela Rampa, Carmela Fimognari, Rolf W Hartmann, Alessandra Bisi
The inhibition of steroidogenic cytochrome P450 enzymes has been shown to play a central role in the management of life-threatening diseases such as cancer, and indeed potent inhibitors of CYP19 (aromatase) and CYP17 (17α hydroxylase/17,20 lyase) are currently used for the treatment of breast, ovarian and prostate cancer. In the last few decades CYP11B1 (11-β-hydroxylase) and CYP11B2 (aldosterone synthase), key enzymes in the biosynthesis of cortisol and aldosterone, respectively, have been also investigated as targets for the identification of new potent and selective agents for the treatment of Cushing's syndrome, impaired wound healing and cardiovascular diseases...
January 30, 2019: Bioorganic Chemistry
Karolina Bachosz, Karol Synoradzki, Maciej Staszak, Manuel Pinelo, Anne S Meyer, Jakub Zdarta, Teofil Jesionowski
Enzymatic cofactor-dependent conversion of monosaccharides can be used in the bioproduction of value-added compounds. In this study, we demonstrate co-immobilization of xylose dehydrogenase (XDH, EC and alcohol dehydrogenase (ADH, EC using magnetite-silica core-shell particles for simultaneous conversion of xylose into xylonic acid (XA) and in situ cofactor regeneration. The reaction conditions were optimized by factorial design, and were found to be: XDH:ADH ratio 2:1, temperature 25 °C, pH 7, and process duration 60 min...
January 29, 2019: Bioorganic Chemistry
Ishani Bhaumik, Kunal Pal, Utsab Debnath, Parimal Karmakar, Kuladip Jana, Anup Kumar Misra
A series of novel analogs of Allicin (S-allyl prop-2-ene-1-sulfinothioate) present in garlic has been synthesized in high yield. Synthesized 23 compounds were evaluated against different breast cancer cells (MDA-MB-468 and MCF-7) and non-cancer cells (WI38). Four compounds (3f, 3h, 3m and 3u) showed significant cytotoxicity against cancer cells whereas nontoxic to the normal cells. Based on the LD50 values and selectivity index (SI), compound 3h (S-p-methoxybenzyl (p-methoxyphenyl)methanesulfinothioate) was considered as most promising anticancer agent amongst the above three compounds...
January 29, 2019: Bioorganic Chemistry
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