25529-64-0Relevant academic research and scientific papers
Synthesis, structural characterisation and anti-proliferative activity of NHC gold amino acid and peptide conjugates
Lemke, Jessica,Pinto, Antonio,Niehoff, Philip,Vasylyeva, Vera,Metzler-Nolte, Nils
, p. 7063 - 7070 (2009)
We report the synthesis of new NHC gold(i) and NHC gold(iii) halide, amino acid and dipeptide complexes. Transmetallation of the N-phenylalanine- substituted NHC silver complex 3 with Me2SAuCl yields the phenylalanine-NHC gold(i) conjugate 4a. Halide exchange with LiBr and oxidation of 4a with Br2 in CH2Cl2 yields the phenylalanine-NHC Au(i) and Au(iii) bromides 4b and 4c, respectively. Reaction of N-Boc protected cysteine methyl ester (Boc-Cys-OMe) or the dipeptide N-Boc-Leu-Cys-OMe with the NHC gold chloride 6a yields the (NHC)Au-S complexed amino acid and dipeptide derivatives 8 and 9. The NHC gold(iii) complexes 4c and 6c were characterised by single crystal X-ray analysis. All of the tested gold carbene complexes showed significant anti-tumor activity on the HeLa, HepG2 and HT-29 cancer cell lines. The best compounds show activity comparable to the well-known anti-cancer drug cisplatin. There seems to be no clear cut structure-activity relationship in the compounds tested, nor did we observe a dependence on the metal oxidation state or the different halide substituents. Given the ease of preparation, stability and high activity of the compounds described herein, it may be possible to design tumor-specific anti-cancer agents based on NHC gold amino acid conjugates in the future.
Post-synthetic functionalization of tryptophan protected peptide sequences through indole (C-2) photocatalytic alkylation
Ackermann, Lutz,Berlinck, Roberto G. S.,Bernardi, Darlon I.,Delgado, José A. C.,Kaplaneris, Nikolaos,Lima, Rafaely N.,Paix?o, Márcio W.
supporting information, p. 5758 - 5761 (2021/06/16)
We report a selective, mild, and efficient C-H functionalization of tryptophan and tryptophan-containing peptides with activated α-bromo-carbonyl compounds under visible-light irradiation. The protocol efficiency is outlined by the wide substrate scope and excellent tolerance of sensitive functional groups present in the amino acid side chains. The method can be successfully extended to access pharmaco-peptide conjugate scaffolds.
Site-Tunable Csp3 -H Bonds Functionalization by Visible-Light-Induced Radical Translocation of N-Alkoxyphthalimides
Wang, Chuanyong,Yu, Yangyang,Liu, Wen-Long,Duan, Wei-Liang
supporting information, p. 9147 - 9152 (2019/11/14)
Site-tunable functionalization of C(sp3)-H bonds has been accomplished through radical translocation and cross-coupling. Upon irradiation with visible light, copper-based photocatalyst [Cu(Xantphos)(dmp)]BF4 enabled cross-coupling of N-alkoxyphthalimides with amino acid esters or amino acids to provide δ-C(sp3)-H alkylated alcohols (31 examples, up to 92% yield) with additive BNDHP or α-C(sp3)-H alkylated alcohols (18 examples, up to 86% yield) with additive DABCO in a highly regioselective fashion.
Synthesis and characterization of selenium(I/II) and tellurium(IV) derivatives of amino acids
Singh, Puspendra,Singh, Harkesh B.,Butcher, Ray J.
supporting information, p. 1 - 9 (2018/09/21)
The direct reaction between Te metal and methyl 2-(2-bromoacetamido)propanoate (27) at room temperature, yields the first example of organotellurium(IV) derivative (MeOC(O)CH(Me)NHCOCH2)2TeBr2 (31). Similarly, reaction of Te with methyl 2-(2-bromoacetamido)acetate (26) and methyl 2-(2-bromoacetamido)-3-phenylpropanoate (28) in presence of NaI in acetone gives MeOC(O)CH2NHCOCH2I (29), MeOC(O)CH(R)NHCOCH2)2TeI2 (R = H (30) and CH2Ph (32). Treatment of 26/27/28 with Li2Te2/Li2Se2 readily provides the [MeOC(O)CH(CH3)NHCOCH2]2Te2, (33); [MeOC(O)CH2NHCOCH2]2Se2, (34); [MeOC(O)CH(CH2Ph)NHCOCH2]2Se2, (35) and [Figure presented] (36). Similarly the reaction of (2,6-dimethyl-4-tert-butylC6H2)SeNa with 28 readily provide the [MeOC(O)CH(CH2Ph)NHCOCH2]SeC6H2-2,6-dimethyl-4-tert-butyl), (37) in good yield. Molecule [MeOC(O)CHNH(Boc)CH2]2Se2, (38) and [NaOC(O)CHNH(Boc)CH2Te(2,4,6-Me3C6H2] (39) were prepared by the treatment of Li2Se2/2,4,6-Me3C6H2TeNa with methyl 3-bromo-2-((tert-butoxycarbonyl)amino)propanoate and N-(t-Boc)-L-serine β-lactone respectively. These compounds are purified by chromatography and characterized by a number of analytical techniques such as (1H, 13C, 77Se and 125Te NMR) spectroscopy, mass spectrometry and elemental analysis. The single crystal X-ray studies of 29, 30, 31, 36 and 38 revealed the presence of characteristic O?Se/Te, secondary bonding interactions. A detailed analysis of the crystal structures of the compound reveals interesting supramolecular assembly.
1,2,3-TRIAZOLE-BASED PEPTIDOMIMETIC INTEGRIN INHIBITORS FOR THE DIAGNOSIS AND THERAPY OF TUMORS
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Page/Page column 25, (2011/09/15)
The present invention refers to the field of chemical compounds bearing a 1,2,3-triazole ring of formula (I) and possessing guanidino and carboxylic groups or their isosteres, their preparation by Cu-catalyzed "click-chemistry", and medical - diagnostic use in pathologies where angiogenesis is altered, for example pathologic conditions of tumor origin, tumor metastasis, osteoporosis, and rheumatoid arthritis.
Click-chemistry-derived triazole ligands of arginine-glycine-aspartate (RGD) integrins with a broad capacity to inhibit adhesion of melanoma cells and both in vitro and in vivo angiogenesis
Trabocchi, Andrea,Menchi, Gloria,Cini, Nicoletta,Bianchini, Francesca,Raspanti, Silvia,Bottoncetti, Anna,Pupi, Alberto,Calorini, Lido,Guarna, Antonio
supporting information; experimental part, p. 7119 - 7128 (2010/11/18)
A click chemistry approach was applied for the discovery of triazole-based arginine-glycine-aspartate (RGD) mimetics by Cu(I)-catalyzed 1,3-dipolar alkyne-azide coupling reaction, which showed binding affinity properties toward αvβ3/αvβ5 integrins. Biological assays showed compound 18 capable of binding αvβ3 integrin with nanomolar affinity according to a two-sites model, and molecular modeling studies revealed a peculiar π-stacking interaction between the triazole ring and Tyr178 side chain. Accordingly, compound 18 inhibited the adhesion of integrin-expressing human melanoma cells to RGD-containing proteins of the extracellular matrix, such as vitronectin, fibronectin, and osteopontin, and also angiogenesis in in vitro and in vivo experimental models. The relevant biological effects exerted by compound 18 suggest its potential application as an antiangiogenic agent in the diagnosis and therapy of tumors where αvβ3 integrin expression is up-regulated.
Design and synthesis of N-methylmaleimide indolocarbazole bearing modified 2-acetamino acid moieties as Topoisomerase I inhibitors
Li, Zhiyu,Zhai, Fuming,Zhao, Li,Guo, Qinglong,You, Qidong
scheme or table, p. 406 - 409 (2011/02/26)
A novel series of N-methylmaleimide indolocarbazole derivatives bearing modified 2-acetamino acid moieties are first reported. The cytotoxic effects of these compounds were tested in five human tumor cell lines. The potent compounds 9a, 9b, 9d, and 9e have been further evaluated for their effect on Topoisomerase I (TOPO I) and cancer cell cycle. It is concluded that the indolocarbazoles with alkyl piperazine or morpholine substituent groups instead of esters or glycosyl residues would have better activities against tumors.
Efficient synthesis of modular amino acid derivatives containing selenium with pronounced GPx-like activity
Alberto, Eduardo E.,Soares, Letiere C.,Sudati, Jessie H.,Borges, Antonio C.A.,Rocha, Joao B.T.,Braga, Antonio L.
supporting information; experimental part, p. 4211 - 4214 (2011/02/22)
New chiral selenide- and diselenide amino acid derivatives have been synthesized. By a simple and efficient two-step route, these new compounds were obtained from inexpensive and commercially available L-amino acids. The products, with a highly modular ch
Value of zeolites in asymmetric induction during photocyclization of pyridones, cyclohexadienones and naphthalenones
Sivasubramanian, Karthikeyan,Kaanumalle, Lakshmi S.,Uppili, Sundararajan,Ramamurthy
, p. 1569 - 1576 (2008/02/05)
Two strategies, namely chiral inductor and chiral auxiliary approaches, have been examined within zeolites with the aim of achieving asymmetric induction during the photocyclization of cyclohexadienone, naphthalenone and pyridone derivatives. Within zeoli
Determination of the absolute stereochemistry of Etzionin
Vaz, Esther,Fernandez-Suarez, Miryam,Munoz, Luis
, p. 1935 - 1942 (2007/10/03)
The absolute configuration of Etzionin, a marine peptide-like compound isolated in 1989 from a red tunicate collected from the Red Sea has been determined by a combination of synthetic and spectroscopic procedures. Finally, its absolute stereochemistry ha
