67865-71-8Relevant academic research and scientific papers
Selectivity profiling of DegP substrates and inhibitors
Hauske, Patrick,Meltzer, Michael,Ottmann, Christian,Krojer, Tobias,Clausen, Tim,Ehrmann, Michael,Kaiser, Markus
, p. 2920 - 2924 (2009)
Protein quality control factors are involved in many key physiological processes and severe human diseases that are based on misfolding or amyloid formation. Prokaryotic representatives are often virulence factors of pathogenic bacteria. Therefore, protein quality control factors represent a novel class of drug targets. The bacterial serine protease DegP, belonging to the widely conserved family of HtrA proteases, exhibits unusual structural and functional plasticity that could be exploited by small molecule modulators. However, only one weak synthetic peptide substrate and no inhibitors are available to date. We report the identification of a potent heptameric pNA-substrate and chloromethyl ketone based inhibitors of DegP. In addition, specificity profiling resulted in the identification of one strong inhibitor and a potent substrate for subtilisin as well as a number of specific elastase substrates and inhibitors.
Design, Synthesis, and Cytotoxic Activity of New Tubulysin Analogues
Le, Hai Van,Tran, Loc Van,Tran, Anh Tuan,Tran, Thao Thi Phuong,Tran, Sung Van,Tran, Chien Van
supporting information, p. 187 - 195 (2021/12/03)
Synthesis of tubulysin analogues, containing an N-methyl substituent on tubuvaline-amide together with the replacement of either the hydrophobic N-terminal N-methyl pipecolic acid (Mep) or at both N- and C- terminal peptides with available heteroaromatic
Amine compound for inhibiting SSAO/VAP-1 and application thereof in medicines
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Paragraph 0392; 0393; 0397; 0398, (2018/09/08)
The present invention relates to an amine compound for inhibiting SSAO/VAP-1 and application thereof in medicines. In particular, the present invention relates to an amine compound for inhibiting a semicarbazide-sensitive oxidase (SSAO) and/or vascular adhesion protein-1 (VAP-1) inhibitor, or a pharmaceutically acceptable salt thereof, a stereoisomer or an/a E/Z isomer, further relates to a pharmaceutical composition containing the amine compound. The invention further relates to the application of the amine compound and the pharmaceutical composition in manufacture of the medicines for treatment of inflammation, inflammation-related diseases and immune diseases.
One-pot synthesis of orthogonally protected dipeptide selenazoles employing Nα-amino selenocarboxamides and α-bromomethyl ketones
Madhu, Chilakapati,Panguluri, Nageswara Rao,Narendra,Panduranga,Sureshbabu, Vommina V.
supporting information, p. 6831 - 6835 (2015/01/09)
A simple and efficient protocol for the synthesis of selenazole containing dipeptidomimetics using Nα-amino selenocarboxamides and α-bromomethyl ketones is described. All the compounds made were isolated in good yields and fully characterized.
Antiplasmodial activity of new 4-aminoquinoline derivatives against chloroquine resistant strain
Sinha, Manish,Dola, Vasanth R.,Agarwal, Pooja,Srivastava, Kumkum,Haq, Wahajul,Puri, Sunil K.,Katti, Seturam B.
, p. 3573 - 3586 (2014/07/07)
Emergence and spread of multidrug resistant strains of Plasmodium falciparum has severely limited the antimalarial chemotherapeutic options. In order to overcome the obstacle, a set of new side-chain modified 4-aminoquinolines were synthesized and screened against chloroquine-sensitive (3D7) and chloroquine-resistant (K1) strains of P. falciparum. The key feature of the designed molecules is the use of methylpiperazine linked α, β3- and γ-amino acids to generate novel side chain modified 4-aminoquinoline analogues. Among the evaluated compounds, 20c and 30 were found more potent than CQ against K1 and displayed a four-fold and a three-fold higher activity respectively, with a good selectivity index (SI = 5846 and 11,350). All synthesized compounds had resistance index between 1.06 and >14.13 as against 47.2 for chloroquine. Biophysical studies suggested that this series of compounds act on heme polymerization target.
CuI-promoted one-pot synthesis of N-boc protected β-ketotriazole amino acids: Application in the synthesis of new class of dipeptidomimetics
Vishwanathaa,Narendra,Sureshbabu, Vommina V.
experimental part, p. 308 - 314 (2012/07/17)
One-pot click chemistry of Nα-Boc-bromomethylketones, NaN3 and propiolic acid affords N-Boc protected 1,4- disubstituted 1,2,3-β-ketotriazole acids in good to excellent yield. The use of CuI as catalyst and DMSO as solvent leads the click react
Structural characterization of folded pentapeptides containing centrally positioned β(R)Val, γ(R)Val and γ(S)Val residues
Dinesh, Bhimareddy,Basuroy, Krishnayan,Shamala, Narayanaswamy,Balaram, Padmanabhan
experimental part, p. 4374 - 4380 (2012/07/28)
A cylindrical pore of ～7.5 diameter containing a one-dimensional water wire, within the confines of a hydrophobic channel lined with the valine side chain, has been observed in crystals of the peptide Boc-d-Pro-Aib-Val-Aib-Val- OMe (1) (Raghavender et al., 2009, 2010). The synthesis and structural characterization in crystals of three backbone homologated analogues Boc-d-Pro-Aib-β3(R)Val-Aib-Val-OMe (2), Boc-d-Pro-Aib- γ4(R)Val-Aib-Val-OMe (3), Boc-d-Pro-Aib-γ4(S) Val-Aib-Val-OMe (4) are described. Crystal structures of peptides 2, 3 and 4 reveal close-packed arrangements in which no pore was formed. In peptides 2 and 3 the N-terminus d-Pro-Aib segment adopted conformations closely related to Type II′ β-turns, while residues 2-4 form one turn of an αβ right-handed C11 helix in 2 and an αγ C12 helix in 3. In peptide 4, a continuous left-handed helical structure was observed with the d-Pro-Aib segment forming a Type III′ β-turn, followed by one turn of a left-handed αγ C12 helix.
Synthesis of N-urethane protected α-aminoalkyl-α-cyanomethyl ketones; Application to the synthesis of 3-substituted 5-amino-1H-pyrazole tethered peptidomimetics
Sharnabai,Nagendra,Sureshbabu, Vommina V.
scheme or table, p. 1913 - 1918 (2012/09/25)
The preparation of N-protected amino/peptide α-cyanomethyl ketones through cyanation of the corresponding α-bromomethyl ketones is described. The utility of the resulting α-cyanomethyl ketones in the synthesis of 3-substituted-5-amino-1H-pyrazoles has also been demonstrated. In both steps a wide range of N-protected amino/peptide acids has been employed and the products are obtained in good yield. The enantiomeric purity of both the α-cyanomethyl ketones and pyrazoles were confirmed by chiral HPLC analysis of the corresponding Z-protected d- and l-Ala-OH as model substrates. The synthesis of peptide pyrazolecarboxamides is also delineated. Georg Thieme Verlag Stuttgart · New York.
Ultrasound mediated synthesis of 2-amino-1,3-selenazoles derived from Fmoc/Boc/Z-α-amino acids
Lalithamba, Haraluru S.,Narendra,Naik, Shankar A.,Sureshbabu, Vommina V.
experimental part, p. 77 - 90 (2010/12/19)
A simple and efficient one-pot synthesis of Fmoc/Boc/Z-amino acid derived 2-amino-1,3-selenazoles by the condensation of Nα-urethane protected amino acid derived bromomethyl ketones with selenourea under the influence of ultrasound has been described. Insertion of 2-amino-1,3-selenazole moiety in the side chains of Asp and Glu has also been achieved following the similar protocol. ARKAT USA, Inc.
Homologation of α-amino acids to β-amino acids: 9-Fluorenylmethyl chloroformate as a carboxyl group activating agent for the synthesis of Nα-protected aminoacyldiazomethanes
Kantharaju,Suresh Babu, Vommina V.
, p. 2152 - 2158 (2007/10/03)
An efficient and stereospecific homologation of urethane-protected α-amino acids to β-amino acids by Arndt-Eistert approach using an equimolar mixture of Fmoc-/Boc-/Z-α-amino acid and 9-fluorenylmethyl chloroformate for the acylation of diazomethane synth
