7364-51-4Relevant academic research and scientific papers
Bortezomib congeners induce apoptosis of hepatocellular carcinoma via CIP2A inhibition
Hou, Duen-Ren,Huang, Ann-Chi,Shiau, Chung-Wai,Wang, Chun-Yi,Yu, Hui-Chuan,Chen, Kuen-Feng
, p. 15398 - 15411 (2014/01/17)
CIP2A is an oncoprotein that upregulates p-Akt and promotes cancer cell proliferation and survival. The proteasome inhibitor bortezomib has been shown to reduce CIP2A and lead to cell apoptosis. Here; we modified the functional group of bortezomib to generate a series of novel compounds and conducted a structure-activity relationship (SAR) study. The results showed that compound 1 was able to repress CIP2A expression and cell apoptosis in the same manner as bortezomib, but with less potency in inhibition of proteasome activity. This finding provides a new direction for the design of CIP2A inhibitors.
A convergent approach to synthesis of bortezomib: the use of TBTU suppresses racemization in the fragment condensation
Ivanov, Andrey S.,Zhalnina, Anna A.,Shishkov, Sergey V.
experimental part, p. 7105 - 7108 (2009/12/09)
Bortezomib is a first-in-class therapeutic antineoplastic agent used for treating patients with multiple myeloma and mantle cell lymphoma. In this paper we report an improved method for synthesis of the title compound using a convergent approach. TBTU was
Simple and rapid synthesis of Nα-urethane protected β-amino alcohols and peptide alcohols employing HATU
Surcshbabu, Vommina V.,Sudarshan,Chennakrishnareddy
experimental part, p. 574 - 579 (2009/12/06)
The activation of the Nα--urcihanc protected (Fmoc-/Boc-/Z-/Bsmoc) α-amino acids employing l-[bis(dimethylamino)- methylene]-lH-l,2,3-triazolo-[4,5-6]pyridinium.0hexa-flurophosphate-3-oxide (HATU) followed by reduction of the in situ generated -OAt ester with NaBH 4 results in the corresponding ss-amino alcohols in good yields. This synthesis is the first demonstration of the application of the efficient coupling agent HATU for practical synthesis of ss-amino alcohols. The protocol is general for all common N-protecting groups including the highly base sensitive Bsmoc group. The protocol has also been successfully extended for the synthesis of peptide alcohols.
Efficient synthesis of O-succinimidyl-(tert-butoxycarbonylamino)methyl carbamates derived from α-amino acids accelerated by ultrasound: Application to the synthesis of ureidodipeptides
Sureshbabu, Vommina V.,Sudarshan, Naremaddepalli S.,Kantharaju
, p. 2168 - 2184 (2008/09/21)
The synthesis of O-succinimidyl-(tert-butoxycarbonylamino)methyl carbamates employing isocyanates made through the Curtius rearrangement of Boc-amino acid azides in the presence of N-hydroxysuccinimide under the influence of ultrasound is described. Copyright Taylor & Francis Group, LLC.
HOBt·DCHA-mediated synthesis of sterically hindered peptides employing Fmoc-amino acid chlorides in both solution-phase and solid phase methods
Sureshbabu, Vommina V.,Sudarshan, Naremaddepalli S.,Chenna Krishna
, p. 2625 - 2637 (2008/12/22)
The synthesis of peptides employing Fmoc-amino acid chlorides in presence of HOBt·DCHA salt in solution as well as by the solid-phase methods is described. The coupling was found to be complete in 30 min and free from racemization. The synthesis of β-casomorphin by solid-phase protocol employing Fmoc-amino acid chloride/HOBt·DCHA in DMF-CH2Cl2 has also been outlined. The final peptide was obtained in 80% yield and was fully characterized. Copyright Taylor & Francis Group, LLC.
ENANTIOPURE HETEROCYCLIC COMPOUND USEFUL FOR THE PREPARATION OF PEPTIDES WHICH CAN BE POTENTIALLY USED AS MEDICAMENTS
-
Page/Page column 17-18, (2008/06/13)
Enantiopure heterocyclic compound Enantiopure heterocyclic compound of formula (I) in which J is chosen from C, N, O and S; Z is H or a group for protecting the amino functional group, R3 denotes H or an organic residue, m is 0, 1 or 2 and n is 0, 1 or 2, and in which the heterocycle is preferably substituted with at least one substituent other than CH2-COOR3.
Preparation, isolation, and characterization of Nα-Fmoc- peptide isocyanates: Solution synthesis of oligo-α-peptidyl ureas
Sureshbabu, Vommina V.,Patil, Basanagoud S.,Venkataramanarao, Rao
, p. 7697 - 7705 (2007/10/03)
(Chemical Equation Presented) The Nα-Fmoc-peptide isocyanates 3a-q, 4a-c, and 5a-c were prepared by the Curtius rearrangement of Nα-Fmoc-peptide acid azides in toluene under thermal, microwave, and ultrasonic conditions. All the Nsu
Synthesis of Fmoc-protected β-amino alcohols and peptidyl alcohols from Fmoc-amino acid/peptide acid azides
Babu, Vommina V. Suresh,Kantharaju,Sudarshan, Naremaddepalli S.
, p. 1880 - 1886 (2007/10/03)
An efficient synthesis of Nα-9H-fluoren-9- ylmethoxycarbony(Fmoc)-β-amino alcohols by the reduction of Fmoc-α-amino acyl azides employing aqueous NaBH4 as a reducing agent has been described. The reduction is found to be simple and almost complete. All the Fmoc-β-amino alcohols prepared are fully characterized by 1H and 13C NMR and mass spectrometry. Further, the method is extended for the reduction of seven Fmoc-dipeptidyl acids to the corresponding alcohols. Their reduction is also found to be smooth and complete.
Synthesis of Nα-protected peptide acids by the N→ C chain extension employing O,N-bis-trimethylsilyl-amino acids using the mixed anhydride method
Tantry, Subramanyam J.,Babu, Vommina V. Suresh
, p. 1282 - 1287 (2007/10/03)
Synthesis of Nα-protected peptide acids employing N→C extension strategy using in situ generated X-NH-CHR′-CO-O-CO- iBu and O,N-bis-trimethylsilyl-amino acids has been accomplished. The coupling is very rapid and efficient. The yield
Chemoenzymatic synthesis of N-Ras lipopeptides
N?gele, Edgar,Schelhaas, Michael,Kuder, Norman,Waldmann, Herbert
, p. 6889 - 6902 (2007/10/03)
For the study of biological phenomena influenced by the plasma-membrane- bound Ras proteins and other lipidated proteins, characteristic peptides which embody the correct lipid modifications of their parent proteins (palmitoyl thioesters and farnesyl thio
