85612-29-9Relevant academic research and scientific papers
Synthesis of (-)-lapatin B
Walker, Steven J.,Hart, David J.
, p. 6214 - 6216 (2007)
The synthesis of (-)-lapatin B (1) has been achieved from l-tryptophan. The key reactions involve oxidative cyclization of N,N-diacetylglyantrypine (8) using PhI(OH)(OTs), and an indole-to-oxindole transformation in the penultimate step.
Guanidine functionalized anthranilamides as effective antibacterials with biofilm disruption activity
Kuppusamy, Rajesh,Yasir, Muhammad,Yee, Eugene,Willcox, Mark,Black, David St. C.,Kumar, Naresh
, p. 5871 - 5888 (2018)
We describe a library of amphiphilic anthranilamide compounds as antimicrobial peptide (AMP) mimics. These contain a hydrophobic naphthoyl side chain and different hydrophilic cationic groups such as amino, quaternary ammonium and guanidino groups. These are prepared via the ring-opening of different isatoic anhydrides. The antibacterial activity against S. aureus and E. coli of compounds containing guanidino cationic groups was greater than that for amino and quaternary ammonium cationic groups. The fluoro-substituted guanidinium compound 9b showed a minimum inhibitory concentration (MIC) of 2.0 μM against S. aureus, and reduced established biofilms of S. aureus by 92% at 64 μM concentration. The bromo-substituted guanidinium compound 9d exhibited good MIC against S. aureus (3.9 μM) and E. coli (15.6 μM) and disrupted established biofilms of S. aureus by 83% at 62.4 μM concentration. Cytoplasmic membrane permeability studies suggested that depolarization and disruption of the bacterial cell membrane could be a possible mechanism for antibacterial activity and the in vitro toxicity studies against MRC-5 human lung fibroblast cells showed that the potent compounds are non-toxic against mammalian cells.
Synthesis of new proteomimetic quinazolinone alkaloids and evaluation of their neuroprotective and antitumor effects
Long, Solida,Resende, Diana I.S.P.,Kijjoa, Anake,Silva, Artur M.S.,Fernandes, Ricardo,Xavier, Cristina P.R.,Vasconcelos, M. Helena,Sousa, Emília,Pinto, Madalena M.M.
, (2019/02/28)
New quinazolinone derivatives of the marine-derived alkaloids fiscalin B (3) and fumiquinazoline G (1), with neuroprotective and antitumor effects, were synthesized. Eleven quinazolinone-containing indole alkaloids were synthesized, proceeding the anti an
Antitumor activity of quinazolinone alkaloids inspired by marine natural products
Long, Solida,Resende, Diana I.S.P.,Kijjoa, Anake,Silva, Artur M.S.,Pina, André,Fernández-Marcelo, Tamara,Helena Vasconcelos,Sousa, Emília,Pinto, Madalena M.M.
, (2018/09/29)
Many fungal quinazolinone metabolites, which contain the methyl-indole pyrazino [1,2-b]quinazoline-3,6-dione core, have been found to possess promising antitumor activity. The purpose of this work was to synthesize the enantiomeric pairs of two members of this quinazolinone family, to explore their potential as antitumor and their ability to revert multidrug resistance. The marine natural product fiscalin B (4c), and antienantiomers (4b, 5b, and 5c) were synthesized via a one-pot approach, while the syn enantiomers (4a, 4d, 5a, and 5d) were synthetized by a multi-step procedure. These strategies used anthranilic acid (i), chiral N-protected α-amino acids (ii), and tryptophan methyl esters (iii) to form the core ring of pyrazino[2,1-b]quinazoline-3,6-dione scaffold. Four enantiomeric pairs, with different enantiomeric purities, were obtained with overall yields ranging from 7 to 40%. Compounds 4a–d and 5a–d were evaluated for their growth inhibitory effect against two tumor cell lines. Differences between enantiomeric pairs were noted and 5a–d displayed GI50 values ranging from 31 to 52 μM, which are lower than those of 4a–d. Nevertheless, no effect on P-glycoprotein (P-gp) modulation was observed for all compounds. This study disclosed new data for fiscalin B (4c), as well as for its analogues for a future development of novel anticancer drug leads.
Synthesis of ent-alantrypinone
Hart,Magomedov
, p. 5892 - 5899 (2007/10/03)
This paper presents a synthesis of ent-alantrypinone (ent-6), the enantiomer of a natural product produced by the fungus Penicillium thymicola. The synthesis revolves around the Li[Me3AlSPh]-promoted isomerization of iminobenzoxazine 33 to quin
Synthesis of (-)-alantrypinone
Hart, David J.,Magomedov, Nabi
, p. 5429 - 5432 (2007/10/03)
A synthesis of (-)-alantrypinone is described. The synthesis features the use of [Me3AlSPh]Li as a promoter of a 4-iminobenzoxazine to 4- quinazolinone rearrangement and as a reagent for the deprotection of an Fmoc- protected amino acid derivat
