57731-07-4Relevant academic research and scientific papers
Mechanistically Guided One Pot Synthesis of Phosphine-Phosphite and Its Implication in Asymmetric Hydrogenation
Sen, Anirban,Kumar, Rohit,Pandey, Swechchha,Vipin Raj,Kumar, Pawan,Vanka, Kumar,Chikkali, Samir H.
supporting information, (2022/01/11)
Although hybrid bidentate ligands are known to yield highly enantioselective products in asymmetric hydrogenation (AH), synthesis of these ligands is an arduous process. Herein, a one pot, atom-economic synthesis of a hybrid phosphine-phosphite (L1) is reported. After understanding the reactivity difference between an O-nucleophile versus C-nucleophile, one pot synthesis of Senphos (L1) was achieved (72 %). When L1 was treated with [Rh], 31P NMR revealed bidentate coordination to Rh. Senphos, in the presence of rhodium, catalyzes the AH of Methyl-2-acetamido-3-phenylacrylate and discloses an unprecedented turn over frequency of 2289, along with excellent enantio-selectivity (92 %). The generality is demonstrated by hydrogenating an array of alkenes. The AH operates under mild conditions of 1–2 bar H2 pressure, at room temperature. The practical relevance of L1 is demonstrated by scaling-up the reaction to 1 g and by synthesizing DOPA, a drug widely employed for the treatment of Parkinson's disease. Computational insights indicate that the R isomer is preferred by 3.8 kcal/mol over the S isomer.
Synthesis, in silico prediction and in vitro evaluation of antimicrobial activity, dft calculation and theoretical investigation of novel xanthines and uracil containing imidazolone derivatives
El-Kalyoubi, Samar,Agili, Fatimah,Zordok, Wael A.,El-Sayed, Ashraf S. A.
, (2021/10/14)
Novel xanthine and imidazolone derivatives were synthesized based on oxazolone derivatives 2a-c as a key intermediate. The corresponding xanthine 3-5 and imidazolone derivatives 6-13 were obtained via reaction of oxazolone derivative 2a-c with 5,6-diaminouracils 1a-e under various conditions. Xanthine compounds 3-5 were obtained by cyclocondensation of 5,6-diaminouracils 1a-c with different oxazolones in glacial acetic acid. Moreover, 5, 6-diaminouracils 1a-e were reacted with oxazolones 2a-c in presence of drops of acetic acid under fused condition yielding the imidazolone derivatives 6-13. Furthermore, Schiff base of compounds 14-16 were obtained by condensing 5, 6-diaminouracils 1a,b,e with 4-dimethylaminobenzaldehyde in acetic acid. The structural identity of the resulting compounds was resolved by IR,1H-,13C-NMR and Mass spectral analyses. The novel synthesized compounds were screened for their antifungal and antibacterial activities. Compounds 3, 6, 13 and 16 displayed the highest activity against Escherichia coli as revealed from the IC50 values (1.8–1.9 μg/mL). The compound 16 displayed a significant antifungal activity against Candia albicans (0.82 μg/mL), Aspergillus flavus (1.2 μg/mL) com-paring to authentic antibiotics. From the TEM microgram, the compounds 3, 12, 13 and 16 exhib-ited a strong deformation to the cellular entities, by interfering with the cell membrane compo-nents, causing cytosol leakage, cellular shrinkage and irregularity to the cell shape. In addition, docking study for the most promising antimicrobial tested compounds depicted high binding affinity against acyl carrier protein domain from a fungal type I polyketide synthase (ACP), and Baumannii penicillin-binding protein (PBP). Moreover, compound 12 showed high drug-likeness, and excellent pharmacokinetics, which needs to be in focus for further antimicrobial drug devel-opment. The most promising antimicrobial compounds underwent theoretical investigation using DFT calculation.
COMPOUNDS AND THEIR SALTS SPECIFIC TO THE PPAR RECEPTORS AND THE EGF RECEPTORS AND THEIR USE IN THE MEDICAL FIELD
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Paragraph 0042; 0043; 0077; 0091, (2013/05/22)
The present invention relates to compounds comprising the general formula (I), in which R1 and R2, which may be identical or different, are selected from the group comprising —H or a linear or branched alkyl group having from 1 to 6 carbon atoms or togeth
Defining the mechanism of action and enzymatic selectivity of psammaplin A against its epigenetic targets
Baud, Matthias G. J.,Leiser, Thomas,Haus, Patricia,Samlal, Sharon,Wong, Ai Ching,Wood, Robert J.,Petrucci, Vanessa,Gunaratnam, Mekala,Hughes, Siobhan M.,Buluwela, Lakjaya,Turlais, Fabrice,Neidle, Stephen,Meyer-Almes, Franz-Josef,White, Andrew J. P.,Fuchter, Matthew J.
scheme or table, p. 1731 - 1750 (2012/04/23)
Psammaplin A (11c) is a marine metabolite previously reported to be a potent inhibitor of two classes of epigenetic enzymes: histone deacetylases and DNA methyltransferases. The design and synthesis of a focused library based on the psammaplin A core has been carried out to probe the molecular features of this molecule responsible for its activity. By direct in vitro assay of the free thiol generated upon reduction of the dimeric psammaplin scaffold, we have unambiguously demonstrated that 11c functions as a natural prodrug, with the reduced form being highly potent against HDAC1 in vitro (IC50 0.9 nM). Furthermore, we have shown it to have high isoform selectivity, being 360-fold selective for HDAC1 over HDAC6 and more than 1000-fold less potent against HDAC7 and HDAC8. SAR around our focused library revealed a number of features, most notably the oxime functionality to be important to this selectivity. Many of the compounds show significant cytotoxicity in A549, MCF7, and W138 cells, with the SAR of cytotoxicity correlating to HDAC inhibition. Furthermore, compound treatment causes upregulation of histone acetylation but little effect on tubulin acetylation. Finally, we have found no evidence for 11c functioning as a DNMT inhibitor.
New synthetic strategies towards psammaplin A, access to natural product analogues for biological evaluation
Baud, Matthias G. J.,Leiser, Thomas,Meyer-Almes, Franz-Josef,Fuchter, Matthew J.
supporting information; experimental part, p. 659 - 662 (2011/03/22)
New synthetic routes towards the natural product psammaplin A were developed with the particular view to preparing diverse analogues for biological assessment. These routes utilize cheap and commercially available starting materials, and allowed access to
Compounds and Their Salts Specific to the PPAR Receptors and the EGF Receptors and Their Use in the Medical Field
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Page/Page column 5-6, (2009/03/07)
The present invention relates to compounds comprising the general formula (I), in which R1 and R2, which may be identical or different, are selected from the group comprising —H or a linear or branched alkyl group having from 1 to 6
Photoisomerization of the green fluorescence protein chromophore and the meta- and para-amino analogues
Yang, Jye-Shane,Huang, Guan-Jhih,Liu, Yi-Hung,Peng, Shie-Ming
, p. 1344 - 1346 (2008/12/21)
The Z → E photoisomerization and fluorescence quantum yields for the wild-type green fluorescence protein (GFP) chromophore (p-HBDI) and its meta- and para-amino analogues (m-ABDI and p-ABDI) in aprotic solvents (hexane, THF, and acetonitrile) and protic
Oxazolones: New tyrosinase inhibitors; synthesis and their structure-activity relationships
Khan, Khalid Mohammed,Mughal, Uzma Rasool,Khan, Mahmud Tareq Hassan,Zia-Ullah,Perveen, Shahnaz,Iqbal Choudhary, Muhammad
, p. 6027 - 6033 (2007/10/03)
The tyrosinase inhibitory potential of seventeen synthesized oxazolone derivatives has been evaluated and their structure-activity relationships developed in the present work. All the synthesized derivatives, 3-19, demonstrated excellent in vitro tyrosina
Deracemisation of aryl substituted α-hydroxy esters using Candida parapsilosis ATCC 7330: Effect of substrate structure and mechanism
Baskar,Pandian,Priya,Chadha, Anju
, p. 12296 - 12306 (2007/10/03)
Candida parapsilosis ATCC 7330 was found to be an efficient biocatalyst for the deracemisation of aryl α-hydroxy esters (65-85% yield and 90-99% ee). A variety of aryl and aryl substituted α-hydroxy esters were synthesized to reflect steric and electronic effects on biocatalytic deracemisation. The mechanism of this biocatalytic deracemisation was found to be stereoinversion.
Solid support Erlenmeyer synthesis of azlactones using microwaves
Mogilaiah,Prashanthi,Reddy, Ch. Srinivas
, p. 2126 - 2128 (2007/10/03)
A rapid and efficient protocol for the synthesis of azlactones is reported starting from acetyl/benzoylglycine and various aromatic aldehydes in the presence of acetic anhydride and sodium acetate in dry media using silica gel as solid support under microwave irradiation. The mild conditions, excellent yields, high purity. short reaction time and easy work-up are some of the major advantages of this method.
