33640-67-4Relevant academic research and scientific papers
Synthesis, experimental and theoretical photophysical study of proton transfer based oxazoline fluorophores. Potential tailor made optical sensors for enantiomeric detection in solution
Santos, Fabiano S.,Zanotto, Gabriel M.,Argomedo, Luis M.Z.,Darbem, Mariana P.,Gon?alves, Paulo F.B.,Stefani, Helio A.,Rodembusch, Fabiano S.
, p. 372 - 382 (2019)
A series of oxazoline based compounds was obtained via amidation formation from salicylic acid derivatives and benzyl-protected L-threonine with good yields (50–90%). These compounds present absorption in the UV region (～300 nm) and fluorescence emission
Use of remote acyl groups for stereoselective 1,2-: Cis -glycosylation with fluorinated glucosazide thiodonors
?ervenková ??astná, Lucie,Cu?ínová, Petra,Dra?ínsky, Martin,Hamala, Vojtěch,Karban, Jind?ich,Kurfi?t, Martin
, p. 5427 - 5434 (2020)
Fluorinated glycans are valuable probes for studying carbohydrate-protein interactions at the atomic level. Glucosamine is a ubiquitous component of glycans, and the stereoselective synthesis of α-linked fluorinated glucosamine is a challenge associated with the chemical synthesis of fluorinated glycans. We found that introducing a 6-O-acyl protecting group onto 3-fluoro and 4-fluoro glucosazide thiodonors endowed them with moderate α-selectivity in the glycosylation of carbohydrate acceptors, which was further improved by adjusting the acceptor reactivity via O-benzoylation. Excellent stereoselectivity was achieved for 3,6-di-O-acyl-4-fluoro analogues. The glycosylation of threonine-derived acceptors enabled the stereoselective synthesis of the protected fluorinated analogue of α-GlcNAc-O-Thr, a moiety abundant in cell-surface O-glycans of the protozoan parasite Trypanosoma cruzi. DFT calculations supported the involvement of transient cationic species which resulted from the stabilization of the oxocarbenium ion through O-6 acyl group participation. This journal is
Synthesis, antitumor activity and in silico analyses of amino acid derivatives of artepillin C, drupanin and baccharin from green propolis
Rodrigues, Débora Munhoz,Portapilla, Gisele Bulh?es,Silva, Guilherme Martins,Duarte, Andressa,Rotta, Cristiana Gon?alez,da Silva, Carlos Henrique Tomich de Paula,de Albuquerque, Sérgio,Bastos, Jairo Kenupp,Campo, Vanessa Leiria
, (2021/08/30)
Breast cancer has the highest incidence and mortality in females, while prostate cancer has the second-highest incidence in males. Studies have shown that compounds from Brazilian green propolis have antitumor activities and can selectively inhibit the AKR1C3 enzyme, overexpressed in hormone-dependent prostate and breast tumors. Thus, in an attempt to develop new cytotoxic inhibitors against these cancers, three prenylated compounds, artepillin C, drupanin and baccharin, were isolated from green propolis to synthesize new derivatives via coupling reactions with different amino acids. All obtained derivatives were submitted to antiproliferative assays against four cancer cells (MCF-7, MDA MB-231, PC-3, and DU145) and two normal cell lines (MCF-10A and PNT-2) to evaluate their cytotoxicity. In general, the best activity was observed for compound 6e, derived from drupanin, which exhibited half-maximal inhibitory concentration (IC50) of 9.6 ± 3 μM and selectivity index (SI) of 5.5 against MCF-7 cells. In silico studies demonstrated that these derivatives present coherent docking interactions and binding modes against AKR1C3, which might represent a possible mechanism of inhibition in MCF-7 cells.
Stereoselective synthesis of natural and non-natural thomsen-nouveau antigens and hydrazide derivatives
Shaik, Ahmad Ali,Nishat, Sharmeen,Andreana, Peter R.
, p. 2582 - 2585 (2015/06/16)
A selective glycosylation strategy enabling access to all stereochemical combinations of tumor associated Thomsen-nouveau (Tn) antigen, d-GalNAc-O-Ser/Thr, has been developed. The key component for selectivity is the phthalimide-protected d- or l-amino acid acceptors which allow access to α- or β-anomers in excellent yields (72-96%) and selectivity (～100%) when appropriate C-2 substitution is installed. The glycoamino acid intermediates were divergently converted to Tn-based carboxylates or to hydrazides by tandem Pd-C debenzylation followed by treatment with hydrazine hydrate or hydrazine hydrate treatment alone.
Concise synthesis of α-methylene-β-hydroxy-γ-carboxy- γ-lactams
Tekkam, Srinivas,Johnson, Joseph L.,Jonnalagadda, Subash C.,Mereddy, Venkatram R.
, p. 955 - 958 (2013/08/23)
A concise protocol for the synthesis of α-methylene-β-hydroxy- γ-carboxy-γ-lactams has been described via alkylation of amino acid derived iminoesters with α-bromomethylmethacrylate, followed by allylic hydroxylation. All the synthesized compounds have been evaluated for their cytotoxicity on multiple myeloma cancer cell lines.
Total synthesis of pactamycin and pactamycate: A detailed account
Hanessian, Stephen,Vakiti, Ramkrishna Reddy,Dorich, Stéphane,Banerjee, Shyamapada,Deschênes-Simard, Beno?t
, p. 9458 - 9472 (2013/01/15)
This article describes synthetic studies that culminated in the first total synthesis of pactamycin and pactamycate and, in parallel, the two known congeners, de-6-MSA-pactamycin and de-6-MSA-pactamycate, lacking the 6-methylsalicylyl moiety. Starting with l-threonine as a chiron, a series of stereocontrolled condensations led to a key cyclopentenone harboring a spirocyclic oxazoline. A series of systematic functionalizations led initially to the incorrect cyclopentanone epoxide, which was "inverted" under solvolytic conditions. Installation of the remaining groups and manipulation of the oxazoline eventually led to pactamycin, pactamycate, and their desalicylyl analogues.
Influence of steric parameters on the synthesis of tetramates from α-amino-β-alkoxy-esters and Ph3PCCO
Loke, Inga,Park, Natja,Kempf, Karl,Jagusch, Carsten,Schobert, Rainer,Laschat, Sabine
supporting information; experimental part, p. 697 - 704 (2012/01/05)
α-Aminoesters react with Ph3PCCO in a domino addition-Wittig cyclization sequence affording enantiomerically pure tetramates. In the case of β-oxo functionalized α-aminoesters, e.g., esters of serine, threonine or β-hydroxyornithine the yields of this reaction depend heavily on the bulkiness of the β-OR group and on the configuration of β-carbon atom C-3. Smaller residues and 2R/3R-configured aminoesters give better yields. The alkoxycarbonyl group of the ester moiety and the residue on the N-atom are less important. These findings can be accounted for by assuming an early puckered transition state for the intramolecular ring-closing Wittig reaction. The addition of sub-stoichiometric amounts of benzoic acid or N-hydroxysuccinimide (for acid-sensitive compounds) is advantageous in some cases as it accelerates the formation of the intermediate amide ylides.
Design, synthesis and the effect of 1,2,3-triazole sialylmimetic neoglycoconjugates on Trypanosoma cruzi and its cell surface trans-sialidase
Campo, Vanessa L.,Sesti-Costa, Renata,Carneiro, Zumira A.,Silva, Jo?o S.,Schenkman, Sergio,Carvalho, Ivone
experimental part, p. 145 - 156 (2012/02/15)
This work describes the synthesis of a series of sialylmimetic neoglycoconjugates represented by 1,4-disubstituted 1,2,3-triazole-sialic acid derivatives containing galactose modified at either C-1 or C-6 positions, glucose or gulose at C-3 position, and by the amino acid derivative 1,2,3-triazole fused threonine-3-O-galactose as potential TcTS inhibitors and anti-trypanosomal agents. This series was obtained by Cu(I)-catalysed azide-alkyne cycloaddition reaction ('click chemistry') between the azido-functionalized sugars 1-N3-Gal (commercial), 6-N 3-Gal, 3-N3-Glc and 3-N3-Gul with the corresponding alkyne-based 2-propynyl-sialic acid, as well as by click chemistry reaction between the amino acid N3-ThrOBn with 3-O-propynyl-GalOMe. The 1,2,3-triazole linked sialic acid-6-O-galactose and the sialic acid-galactopyranoside showed high Trypanosoma cruzi trans-sialidase (TcTS) inhibitory activity at 1.0 mM (approx. 90%), whilst only the former displayed relevant trypanocidal activity (IC50 260 μM). These results highlight the 1,2,3-triazole linked sialic acid-6-O-galactose as a prototype for further design of new neoglycoconjugates against Chagas' disease.
Total synthesis of pactamycin
Hanessian, Stephen,Vakiti, Ramkrishna Reddy,Dorich, Stephane,Banerjee, Shyamapada,Lecomte, Fabien,DelValle, Juan R.,Zhang, Jianbin,Deschenes-Simard, Benoait
supporting information; experimental part, p. 3497 - 3500 (2011/05/12)
Lest we forget: 50 years after pactamycin was first isolated from a fermentation broth of Streptomyces pactum var pactum, this highly functionalized aminocyclopentitol natural product has finally succumbed to total synthesis. The modular and stereocontrolled introduction of functional groups should lead to the synthesis of less toxic congeners that maintain the antibacterial and cytotoxic activities. Copyright
A class of novel conjugates of substituted purine and Gly-AA-OBzl: Synthesis and evaluation of orally analgesic activity
Kang, Guifeng,Zhao, Ming,Zhang, Xiaoyi,Peng, Li,Li, Chunbo,Mao, Wei,Ye, Weidong,Peng, Shiqi
supporting information; experimental part, p. 6157 - 6160 (2010/12/19)
Aimed at the chemotherapy of chronic pain two kinds of analgesic pharmacophores, substituted purine and Gly-AA-OBzl, were coupled via a five-step-reaction procedure and 19 novel conjugates N-[2-chloro-9- (tetrahydropyran-2-yl)-9H-purin-6-yl]-N-cyclopropylglycylamino acid benzylesters were provided. On mouse-tail flick model their in vivo analgesic activities were assayed. The results indicate that introducing Gly-OC2H 5 into the 6-position of the substituted purine leads to ambiguous increase of the analgesic activity, while introducing Gly-AA-OBzl into this position leads to significant increase of the analgesic activity.
