4702-13-0Relevant academic research and scientific papers
Novel method for preparation of monoesters of symmetric diphenolic compounds like curcumin (1,7-bis(4-hydroxy-3-methoxy phenyl)-1,6-heptadiene-3,5- dione) via solid-phase synthesis
Dubey, Shiv Kumar,Dwivedi, Vishnu,Misra, Krishna
, p. 4265 - 4271 (2007)
Synthesis of a monoester of symmetrical diphenolic compound curcumin (1,7-bis(4-hydroxy-3-methoxy phenyl)-1,6-heptadiene-3,5-dione) with glycine has been carried out by anchoring one of its free phenolic groups to an insoluble polymeric solid-support resin controlled pore glass-long chain alkylamine (CPG-LCAA) via a 2-carbon linker by solid-phase synthesis. The other free phenolic was esterified selectively with N-protected glycinoyl chloride to give the monoester exclusively. Subsequent deprotection of the amino group and deblocking of the monoester from polymer support by treatment with hydriodic acid (HI) gave the desired product. We earlier reported synthesis of a large number of diesters of curcumin, but selective esterification of one phenolic has been accomplished by this novel method, which can be used for preparing monoesters of any symmetric diphenol in quantitative yields. Copyright Taylor & Francis Group, LLC.
5,15-diaminotetrabenzoporphyrins: Synthesis and spectral properties
Yakubov,Galanin,Shaposhnikov
, p. 482 - 487 (2012)
A zinc complex of 5,15-di(N-phthalimidyl)tetrabenzoporphyrin was obtained by the reaction of Ncarboxymethylphthalimide with 1-oxo-1H-3-(1-oxoisoindolin-3- ylidenemethyl)isoindole and zinc oxide. The complex demetallation affords 5,15-di(N-phthalimidyl)tetrabenzoporphyrin. The reaction of N- phthalimidylsubstituted tetrabenzoporphyrins with hydrazine hydrate leads to the formation of 5,15-diaminotetrabenzoporphyrins. Spectral properties of these compounds were studied. Pleiades Publishing, Ltd., 2012.
The first example of linear peptides containing a N-trifluoroethylated backbone amide linkage and the surprising solution dynamics observed by 19F NMR
Lu, Changqing,DesMarteau, Darryl D.
, p. 832 - 838 (2007)
The α-amino group of (l)phenylalanine methyl ester was trifluoroethylated using (2,2,2-trifluoroethyl)phenyliodonium N,N-bis(trifluoromethylsulfonyl)imide. A dipeptide Gly(l)Phe containing a trifluoroethylated peptide bond was synthesized by removing the α-amino proton of Nα-trifluoroethyl (l)phenylalanine methyl ester followed by coupling with Nα-phthaloyl glycine acid fluoride. The dipeptide was further coupled with (l)leucine methyl ester under conventional carboxyl activation conditions to provide two diastereomers of the tripeptide Gly(d,l)Phe(l)Leu. The solution dynamic behavior of the tripeptide was investigated as a function of solvents, by NOESY and variable temperature (VT) 19F NMR experiments.
Synthesis and anticonvulsant activities of functionalized 5-(isoindole-1,3-dione)-pyrimidinones
Sharma, Rashmi,Gawande, Dinesh Y.,Mohan, Chander,Goel, Rajesh Kumar
, p. 1420 - 1424 (2016)
The present work involves the synthesis of previously unknown 5-(isoindole-1,3-dione) pyrimidinones by [4?+?2] cycloaddition reactions of functionalized 1,3-diazabuta-1,3-dienes with phthalimidoketene, generated in situ from phthaloylglycine, tosyl chloride, and triethylamine. The 5-(isoindole-1,3-dione)-pyrimidinones have been screened in vivo for their anticonvulsant activities using MES and PTZ methods. A comparative study for in vivo anticonvulsant activities of these functionalized pyrimidinones with a variety of substitutions at different positions was also conducted. 2-(4-Dimethylamino-6-oxo-1,2-diphenyl-1,6-dihydro-pyrimidin-5-yl)-isoindole-1,3-dione has shown the maximum anticonvulsant activities at 100?mg/kg test dose using MES and PTZ tests.
Structural, spectroscopic, nonlinear optical and electronic properties of calcium N-phthaloylglycinate: A combined experimental and theoretical study
Tamer, ?mer,Bhatti, Moazzam H.,Yunus, Uzma,Avc?, Davut,Atalay, Yusuf,Nadeem, Muhammad,Shah, Syed Raza,Helliwell, Madeleine
, p. 315 - 322 (2016)
A calcium complex of N-phthaloylglycine (CaNPG) has been synthesized, and its crystal structure has been characterized by X-ray diffraction method. The FT-IR and fluorescence spectra for CaNPG have been recorded. N-phthaloylglycine ligand coordinates to Ca ion through the carboxylate O atoms as a bidentate ligand, and Ca ion does not play an important role in florescence spectrum. In order to support experimental findings and also investigate molecular surfaces, natural bond orbital (NBO) and nonlinear optical (NLO) optical properties of CaNPG complex, density functional theory calculations have been performed by hybrid B3LYP level. The very small energy gap between α-spin frontier molecular orbitals (FMOs) is demonstrated that CaNPG is a very reactive, chemically soft and optically active complex. The high stabilization energies of hyperconjugative interactions are also demonstrate that the charge mobility in CaNPG is very high. As consistent with above findings, first static hyperpolarizability of CaNPG has been found to be 10 times higher than pNA which is a NLO material.
A trio of quinoline-isoniazid-phthalimide with promising antiplasmodial potential: Synthesis, in-vitro evaluation and heme-polymerization inhibition studies
Rani, Anu,Sharma, Anny,Legac, Jenny,Rosenthal, Philip J.,Singh, Parvesh,Kumar, Vipan
, (2021)
Quinoline-isoniazid-phthalimide triads have been synthesised to assess their antiplasmodial efficacy and cytotoxicity against chloroquine-resistant W2 strain of P. falciparum and Vero cells, respectively. Most of the synthesized compounds displayed IC50 in lower nM range and appeared to be approximately five to twelve fold more active than chloroquine. Heme-binding studies were also carried out to delineate the mode of action. The promising compounds with IC50s in range of 11–30 nM and selectivity index >2800, may act as promising template for the design of new antiplasmodials.
Hg2+-selective "turn-on" fluorescent chemodosimeter derived from glycine and living cell imaging
Mahapatra, Ajit Kumar,Roy, Jagannath,Manna, Saikat Kumar,Kundu, Supratim,Sahoo, Prithidipa,Mukhopadhyay, Subhra Kanti,Banik, Avishek
, p. 26 - 32 (2012)
A new nonfluorescent benzthiazole derivative of dithio-N-phthaloylglycine was prepared, and its fluorogenic chemodosimetric behaviors toward transition metal ions were investigated. The dithio-N-phthaloylglycine derivative showed highly Hg2+-selective fluorescence enhancing ("turn-on") properties in 20% aqueous acetonitrile solution (H2O/CH3CN = 80:20, v/v). The chemodosimetric behavior is based on the Hg2+ triggered desulfurization of dithio-N-phthaloylglycine derivative into its oxygen analogue. To observe the cell permeability of 3 into Pollen grains, we also employed it for the fluorescence detection of the changes of intracellular Hg2+ in cultured cells.
Design and synthesis of 4-Aminoquinoline-isoindoline-dione-isoniazid triads as potential anti-mycobacterials
Rani, Anu,Johansen, Matt D.,Roquet-Banères, Fran?oise,Kremer, Laurent,Awolade, Paul,Ebenezer, Oluwakemi,Singh, Parvesh,Sumanjit,Kumar, Vipan
, (2020)
A series of 4-aminoquinoline-isoindoline-dione-isoniazid triads were synthesized and assessed for their anti-mycobacterial activities and cytotoxicity. Most of the synthesized compounds exhibited promising activities against the mc26230 strain of M. tuberculosis with MIC in the range of 5.1–11.9 μM and were non-cytotoxic against Vero cells. The conjugates lacking either isoniazid or quinoline core in their structural framework failed to inhibit the growth of M. tuberculosis; thus, further strengthening the proposed design of triads in the present study.
The switch-on luminescence sensing of histidine-rich proteins in solution: A further application of a Cu2+ ligand
Wang, Bin,Gao, Yang,Li, Hong-Wei,Hu, Zhi-Peng,Wu, Yuqing
, p. 4032 - 4034 (2011)
A new probe/Cu2+ complex for the detection of his-tagged protein has been developed, based on an improved probe, Dansyl-Gly-Py (1), by closely mimicing the structure of a peptide, ATCUN. In aqueous solution, 1/Cu 2+ has good selectivity to histidine and cysteine, and further can detect histidine-rich protein by releasing the quenched fluorescence of 1.
Amino acid conjugates of aminothiazole and aminopyridine as potential anticancer agents: Synthesis, molecular docking and in vitro evaluation
Ali, Tahir,Imran, Muhammad,Li, Jing Bo,Li, Shupeng,Nadeem, Humaira,Naz, Shagufta,Sarwar, Sadia,Shah, Fawad Ali,Tan, Zhen
, p. 1459 - 1476 (2021/04/19)
Purpose: The development of resistance to available anticancer drugs is increasingly becoming a major challenge and new chemical entities could be unveiled to compensate this therapeutic failure. The current study demonstrated the synthesis of 2-aminothiazole [S3 (a-d) and S5(a-d)] and 2-aminopyridine [S4(a-d) and S6(a-d)] derivatives that can target multiple cellular networks implicated in cancer development. Methods: Biological assays were performed to investigate the antioxidant and anticancer potential of synthesized compounds. Redox imbalance and oxidative stress are hallmarks of cancer, therefore, synthesized compounds were preliminarily screened for their antioxidant activity using DPPH assay, and further five derivatives S3b, S3c, S4c, S5b, and S6c, with significant antioxidant potential, were selected for investigation of in vitro anticancer potential. The cytotoxic activities were evaluated against the parent (A2780) and cisplatin-resistant (A2780CISR) ovarian cancer cell lines. Further, Molecular docking studies of active compounds were performed to determine binding affinities. Results: Results revealed that S3c, S5b, and S6c displayed promising inhibition in cisplatin-resistant cell lines in comparison to parent cells in terms of both resistance factor (RF) and IC50 values. Moreover, S3c proved to be most active compound in both parent and resistant cell lines with IC50 values 15.57 μM and 11.52 μM respectively. Our docking studies demonstrated that compounds S3c, S5b, and S6c exhibited significant binding affinity with multiple protein targets of the signaling cascade. Conclusion: Anticancer activities of compounds S3c, S5b, and S6c in cisplatin-resistant cell lines suggested that these ligands may contribute as lead compounds for the development of new anticancer drugs.
