4702-13-0Relevant articles and documents
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.
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.
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.
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.
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.
Synthesis method N -phthalimide-based acetic acid
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Paragraph 0011; 0012-0024, (2021/09/11)
The invention discloses a synthesis method of N -phthalimide-based acetic acid. Based on N - hydroxyethyl phthalimide as a base, N -hydroxyphthalimide (NOP) was used as a catalyst, and N - phthalimide-based acetic acid was obtained by air oxidation. The mass of the catalyst NOP is N - of the mass of 1 - 10% hydroxyethyl phthalimide, the reaction employs cyclohexane as a solvent, and the mass of the solvent is N - times the mass of 20 - 50 hydroxyethyl phthalimide. The reaction temperature was between 50 and 100 °C, the air ventilation rate was 1L/seconds, and the aeration time was 5 - 48 hours. The method replaces the toxic raw materials such as toluene used in the prior literature report. The production is reduced. The method has the advantages of low management cost, mild reaction conditions and low production cost.
Potent antiproliferative activity of bradykinin B2 receptor selective agonist FR-190997 and analogue structures thereof: A paradox resolved?
Rassias, Gerasimos,Leonardi, Sofia,Rigopoulou, Dionisia,Vachlioti, Eleanna,Afratis, Konstantinos,Piperigkou, Zoi,Koutsakis, Christos,Karamanos, Nikos K.,Gavras, Haralambos,Papaioannou, Dionissios
supporting information, (2020/11/12)
Βradykinin stimulation of B2 receptor is known to activate the oncogenic ERK pathway and overexpression of bradykinin receptors B1 and B2 has been reported to occur in glioma, colorectal and cervical cancers. B1R and B2R antagonists have been shown to reverse tumor proliferation and invasion. Paradoxically, B1R and B2R agonism has also been reported to elicit antiproliferative benefits. In order to complement the data accumulated to date with the natural substrate bradykinin and peptidic B2R antagonists, we decided to examine for the first time the response elicited by B2R stimulation in breast cancer lines with a non-peptidic small molecule B2R agonist. We synthesized and assessed the highly selective and potent B2R partial agonist FR-190997 in MCF-7 and MDA-MBA-231 breast cancer lines and found it possessed significant antiproliferative activity (IC50 2.14 and 0.08 μΜ, respectively). The modular nature of FR-190997 allowed us to conduct a focused SAR study and discover compound 10 which exhibits subnanomolar antiproliferative activity (IC 50 0.06 nΜ) in the TNBC MDA-MBA-231 cell line. This performance surpasses, in most cases by several orders of magnitude, those of established anticancer agents and FDA-approved breast cancer drugs. In line with the established literature we suggest that this remarkable activity precipitates from a dual mode of action involving agonist-induced receptor internalization/degradation combined with sequestration of functional intracellular B2 receptors and inhibition of the associated endosomal signaling. The latter mode may be realized by appropriate ligands regardless of B2R agonist/antagonist designation which only relates to membrane residing GCPRs. Under this prism the controversy over the antiproliferative effects of B2 agonists and antagonists is potentially neutralized.
HETEROCYCLIC COMPOUNDS AS MODULATORS OF STIMULATOR OF INTERFERON GENES (STING)
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Page/Page column 92-93, (2021/06/22)
The present invention relates to compounds of formula (I) and salts, stereoisomers, tautomers or N-oxides thereof that are useful as modulators of STING (Stimulator of Interferon Genes). The present invention further relates to the compounds of formula (I) for use as a medicament and to a pharmaceutical composition comprising said compounds.
