3183-10-6Relevant academic research and scientific papers
DUAL KINASE-BROMODOMAIN INHIBITORS
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, (2021/12/12)
Provided herein are compounds of Formula (I) that are dual inhibitors of kinases and bromo-domain proteins. The disclosure also relates to pharmaceutical compositions containing such compounds, methods for using such compounds in the treatment of cancers, particularly, the treatment of multiple myeloma cancers, and to related uses.
Synthesis of novel phthalimido oxime pseudoesters and evaluation of their cytotoxicity
Mehrez, Asma,Chakroun, Ibtissem,Mtat, Dalila,Mansour, Hédi Ben,Touati, Ridha
, p. 1 - 8 (2020/11/02)
A series of novel optically pure oxime pseudoesters derivatives were synthesized by the reaction of substitute keto oximes with various N-substituted α-amino acids chlorides in the presence of triethylamine and dichloromethane at 0 °C, and their structures were characterized by IR and 1D-NMR methods. The synthesized compounds were tested for their ability to inhibit the proliferation of human colon cancer cells and human epithelial cells. Some of them were revealed to have a significant cytotoxic effect.
1,2-Hydride Migration in Dialkyl α-Diazophosphonates Catalyzed by [Cu(MeCN)4]PF6: A Novel Approach to β-Amino (E)-Enylphosphonates
Ge, Haihong,Liu, Shuang,Cai, Yan,Sun, Yuchao,Miao, Zhiwei
, p. 448 - 454 (2016/01/28)
The regiospecific and stereoselective 1,2-migration reaction of dialkyl α-diazophosphonates for the synthesis of β-amino (E)-enylphosphonates is developed utilizing tetrakis(acetonitrile)copper(I) hexafluorophosphate [Cu(MeCN)4PF6] as the catalyst and N,N-dimethylformamide as an additive. A possible mechanism for the 1,2-migration reaction involving a metal carbene is presented. An investigation on the E/Z isomer selectivity of this process demonstrates that steric factors play an important role on the outcome. This process provides a straightforward access to β-amino (E)-enylphosphonates in moderate to good yields.
Enantiomerically Pure [2.2]Paracyclophane-4-thiol: A Planar Chiral Sulfur-Based Building Block Readily Available by Resolution with an Amino Acid Chiral Auxiliary
Vincent, Adrien,Deschamps, Damien,Martzel, Thomas,Lohier, Jean-Fran?ois,Richards, Christopher J.,Gaumont, Annie-Claude,Perrio, Stéphane
, p. 3961 - 3966 (2016/05/24)
Acyl chloride of N-phthaloyl-(S)-isoleucine is an efficient chiral auxiliary for the resolution of (±)-[2.2]paracyclophane-4-thiol. A preparative protocol, based on the conversion into diastereoisomeric thiolesters and separation by two fractional crystallizations and column chromatography, was developed. Deprotection with LiAlH4 allowed isolation of the individual thiol enantiomers in good yield (～40%) and high enantiomeric purity (ee >93%). The absolute configurations were determined by comparison of the optical rotation value of the products with literature data and were confirmed by X-ray crystallography.
Trifluoroborane-catalyzed C-H functionalization/S-H insertion reaction: Construction of N,S-acetal quaternary centers
Cai, Yan,Ge, Haihong,Sun, Weize,Miao, Zhiwei
, p. 1669 - 1677 (2015/06/02)
Abstract The trifluoroborane-catalyzed C-H functionalization/S-H insertion reaction of α-diazophosphonates with thiols has been developed. A plausible reaction mechanism has been proposed to understand the combined reaction. This process provides straightforward access to N,S-acetals containing quaternary centers in moderate to good yields and chemoselectivity.
Silicon-containing poly(esters) with halogenated bulky side groups. Synthesis, characterization and thermal studies
Tagle,Terraza,Tundidor-Camba,Coll
, p. 49132 - 49142 (2015/06/16)
Poly(esters) (PEs) derived from diacids containing bulky side groups, which have an halogenated (Cl, Br) imide ring, an aminoacidic residue (glycine, l-alanine, l-valine) and an amide group were obtained with a silicon-containing diphenol. Also PEs without the aminoacidic residue were obtained. PEs were characterized by IR and NMR spectroscopy, and the results were in agreement with the proposed structures. PEs were obtained with good yields and moderate or high ηinh values. PEs were soluble in aprotic polar solvents and were swollen in other solvents like m-cresol and THF. The Tg values were determined and it was possible to see a tendency in the sense that when the size of the atom (Cl, Br) bonded to the imidic ring is increased, the Tg values decreased, also for those PEs obtained without the aminoacidic residue. The thermal decomposition temperatures showed that only two PEs can be considered as thermostable, considering TDT values above 400°C at 10% of weight lost. The other PEs showed good thermal stability, showing in general a decrease of the TDT values when the volume of the side group, is increased. PEs showed UV-vis transparency at 400 nm lower than 20%, but between 500 and 600 nm, showed 80% transparency. PEs containing halogen atoms showed flame retardancy in a simple essay, with respect to PEs without halogen atoms in which the combustion was complete.
Chiral Pool-Based Synthesis of Naphtho-Fused Isocoumarins
Raza, Abdul Rauf,Saddiqa, Aisha,?akmak, Osman
, p. 951 - 957 (2015/11/16)
A variety of chiral derivatives of benzo[d]naphtho[1,2-b]pyran-6-one were prepared in a single step by Et3N-mediated condensation of homophthalic anhydride with different derivatives of (S)-amino acid chlorides at -5 °C by employing a chiral pool methodology. Chirality 27:951-957, 2015.
Unexpected stereoselective synthesis of (Z)-β-alkenyl substituted β-amino phosphonates through β,γ-dihydrogen shift reaction catalyzed by a copper(I) complex and iodine [Cu(MeCN)4]PF 6/I2
Cai, Yan,Lyu, Hairong,Yu, Chengbin,Miao, Zhiwei
, p. 596 - 602 (2014/05/20)
A series of dialkyl a-diazophosphonates has been prepared from natural amino acids. The diazo decomposition of these diazophosphonate compounds with tetrakis(acetonitrile)copper(I) hexafluorophosphate/iodine, [Cu(MeCN) 4]PF6/I2, as catalyst has been investigated. It was found that the diazo decomposition of dialkyl a-diazophosphonates gave a mixture of β,γ-dihydrogen shift and 1,2-hydride migration products and afforded β-alk- enyl-substituted β-amino phosphonates with the Z configuration. The mechanism of this novel diazo decomposition process was discussed.
Chiron based synthesis of isocoumarins: Reactivity of α-substituted carboxylic acids
Saddiqa, Aisha,Raza, Abdul R.,Black, David Stc.,Kumar, Naresh
, p. 736 - 743 (2014/06/09)
The asymmetric synthesis of a novel (S)-isocoumarin has been attempted in a single step by the coupling of homophthalic acid with (S)-N-protected amino acids and α-chloroacids at high temperature by exploiting a chiral pool methodology. The coupling of homophthalic acid with N-protected (S)-amino acids gave exclusion of the carboxyl/alkyl group. However, coupling of homophthalic acid with α-chloroacids afforded asymmetric isocoumarins in high yield.
Nonnatural amino acid synthesis by using carbon-hydrogen bond functionalization methodology
Tran, Ly Dieu,Daugulis, Olafs
, p. 5188 - 5191 (2012/07/27)
Taking direction well: Substituted phenylalanine derivatives were prepared by C-H bond functionalization (see scheme). The syntheses are highly convergent and employ an N-phthaloylalanine with a 2-thiomethylaniline directing group. The use of an 8-aminoquinoline directing group allows for the diarylation of methyl and the diastereoselective arylation of methylene groups. Copyright
