Synthesis of a new class of pyrrolo[3,4-h]quinazolines with antimitotic activity

Spanò, Virginia; Montalbano, Alessandra; Carbone, Anna; Parrino, Barbara; Diana, Patrizia; Cirrincione, Girolamo; Castagliuolo, Ignazio; Brun, Paola; Issinger, Olaf‐Georg; Tisi, Silvia; Primac, Irina; Vedaldi, Daniela; Salvador, Alessia; Barraja, Paola

doi:10.1016/j.ejmech.2013.10.014

Cited by 47 publications

(24 citation statements)

References 38 publications

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“…In the framework of our research on polycyclic nitrogen systems, [16,17,18,19,20,21,22,23,24,25,26,27,28,29,30,31,32,33] particularly referring to nortopsentin alkaloid analogues [34,35,36,37,38,39], herein we report the synthesis of the new series of thiazoles 1 (Table 1) and their evaluation as antibiofilm agents. In this series of nortopsentin analogues, the imidazole core of the natural product is replaced by the thiazole ring and one of the indole units is replaced by a 7-aza-indole moiety decorated with an ethanamine chain bound to the imine nitrogen.…”

Section: Introductionmentioning

confidence: 99%

New Thiazole Nortopsentin Analogues Inhibit Bacterial Biofilm Formation

et al. 2018

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New thiazole nortopsentin analogues were conveniently synthesized and evaluated for their activity as inhibitors of biofilm formation of relevant Gram-positive and Gram-negative pathogens. All compounds were able to interfere with the first step of biofilm formation in a dose-dependent manner, showing a selectivity against the staphylococcal strains. The most active derivatives elicited IC50 values against Staphylococcus aureus ATCC 25923, ranging from 0.40–2.03 µM. The new compounds showed a typical anti-virulence profile, being able to inhibit the biofilm formation without affecting the microbial growth in the planktonic form.

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Section: Introductionmentioning

confidence: 99%

New Thiazole Nortopsentin Analogues Inhibit Bacterial Biofilm Formation

et al. 2018

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“…Anticancer agent Iressa (ZD1839) A is a clinically approved example of quinazoline-based inhibitors which is in phase III clinical trials for cancer used to inhibit the receptor tyrosine kinase of epidermal growth factor. also exhibit pronounced biological activities as antimicrobial, 7,8 anti-HIV (NNRTI), 9,10 anti-tumour, [11][12][13][14][15][16] potential analgesic and anti-inflammatory activity. 17 Non-proteinogenic amino acids are major component in a number of drugs including β-lactam antibiotics 18 and glutamate antagonists.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of methyl [3-alkyl-2-(2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl)-acetamido] alkanoate

Ismail¹,

Ali²,

Fathalla³

et al. 2017

Arkivoc

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A series of methyl [3-alkyl-2-(2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl)-acetamido] alkanoate 10-13a-f has been developed on the basis of the N-chemoselective reaction of 3-substituted quinazoline-2,4-diones 3a-d with ethyl chloroacetate and azide coupling method with amino acid ester hydrochloride. The precursor quinazoline diones 3a-d chemoselective reactions were studied using DFT(B3LYP)/6-311G level of theory and were prepared by a new rearrangement method from the corresponding 2-(3-methyl-4-oxo-3,4-dihydroquinazolin-2-ylthio) acetohydrazide 6.

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“…Among various heterocyclic compounds, N ‐heterocyclic compounds are very important in drug design . Compounds containing pyrrolopyrimidine functional groups, collectively referred to as 7‐deazapurines, are a structurally diverse class of nucleoside analogs with demonstrated antibiotic .…”

Section: Introductionmentioning

confidence: 99%

Efficient Synthesis of Pyrrolo [2,3‐d] Pyrimidines Containing 1,4‐Disubstituted‐1,2,3‐Triazole Derivatives

Ruddarraju¹,

Murugulla²,

Donthabakthuni³

et al. 2016

Journal of Heterocyclic Chem

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Here, we demonstrate a simple but highly efficient method for the synthesis of multifunctionalized pyrrolo[2,3‐d]pyrimidines containing 1,4‐disubstituted 1,2,3‐triazole derivative coupled with various amines (10a, 10b, 10c, 10d, 10e, 10f, 10g) and alcohol (10h) to obtain final compounds (11a, 11b, 11c, 11d, 11e, 11f, 11g, 11h) with reasonable to excellent yields (25% to 94%). The newly synthesized compounds were characterized by IR, 1HNMR, 13CNMR, and mass spectroscopy analysis.

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Synthesis of a new class of pyrrolo[3,4-h]quinazolines with antimitotic activity

Cited by 47 publications

References 38 publications

New Thiazole Nortopsentin Analogues Inhibit Bacterial Biofilm Formation

New Thiazole Nortopsentin Analogues Inhibit Bacterial Biofilm Formation

Synthesis of methyl [3-alkyl-2-(2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl)-acetamido] alkanoate

Efficient Synthesis of Pyrrolo [2,3‐d] Pyrimidines Containing 1,4‐Disubstituted‐1,2,3‐Triazole Derivatives

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