591755-14-5Relevant articles and documents
Synthesis and evaluation of new 4(3H)-Quinazolinone derivatives as potential anticancer agents
Gatadi, Srikanth,Pulivendala, Gauthami,Gour, Jitendra,Malasala, Satyaveni,Bujji, Sushmitha,Parupalli, Ramulu,Shaikh, Mujahid,Godugu, Chandraiah,Nanduri, Srinivas
, (2019/09/30)
A series of new 4(3H)-quinazolinones were synthesized and evaluated for their cytotoxic activity against a set of human cancer cell lines MDA-MB-231 and MCF-7 (breast), HCT-116 and HT-29 (colon) and A549 (lung). Among the tested compounds, 22a exhibited p
Late-Stage C-H Arylation of Thiazolo[5,4- f ]quinazolin-9(8 H)-one Backbone: Synthesis of an Array of Potential Kinase Inhibitors
Couly, Florence,Dubouilh-Benard, Carole,Besson, Thierry,Fruit, Corinne
, p. 4615 - 4622 (2017/10/13)
Driven by the need of structural modification to establish structure-activity relationships, the regioselective C-H bond activation of thiazolo[5,4- f ]quinazolin-9(8 H)-one backbone has been developed to furnish the corresponding C2-arylated valuable scaffold. This strategy provides a synthetically streamlined and useful route for late-stage diversification of this attractive skeleton, required in drug discovery. A more eco-friendly synthesis of thiazolo[5,4- f ]quinazolin-9(8 H)-ones is also described giving access to these aforementioned compounds in a facile manner.
Pd-catalyzed and copper assisted regioselective sequential C2 and C7 arylation of thiazolo[5,4-f]quinazolin-9(8H)-one with aryl halides
Harari, Marine,Couly, Florence,Fruit, Corinne,Besson, Thierry
supporting information, p. 3282 - 3285 (2016/07/13)
A selective functionalization of thiazolo[5,4-f]quinazolin-9(8H)-one has been developed through sequential activation of C-H bonds to furnish diarylated compounds. This strategy allows the regioselective C2 and C7 arylation by a judicious choice of coupling partners and bases, requiring no additional ligands or directing groups. Differently substituted N8-benzylated-2,7-diaryl-thiazoloquinazolin-9(8H)-ones were thereby obtained in a facile manner. A one-pot procedure was also performed. These protocols provide a synthetically useful route for late-stage functionalization of this highly valuable scaffold, required in drug discovery.
Novel synthesis of angular thiazolo[5,4-f] and [4,5-h]quinazolines, preparation of their linear thiazolo[4,5-g] and [5,4-g]quinazoline analogs
Hédou, Damien,Guillon, Rémi,Lecointe, Charlotte,Logé, Cédric,Chosson, Elizabeth,Besson, Thierry
, p. 3182 - 3191 (2013/04/24)
Synthesis of 9-oxo-8,9-dihydrothiazolo[5,4-f]quinazoline-2-carbonitrile (1) or 6-oxo-6,7-dihydrothiazolo[4,5-h]quinazoline-2-carbonitrile (2) was reinvestigated with the ambition of varying the position of the thiazole ring linked to the quinazolin-4-one
Non-classical antifolates. Part 2: Synthesis, biological evaluation, and molecular modeling study of some new 2,6-substituted-quinazolin-4-ones
Al-Omary, Fatmah A.M.,Abou-zeid, Laila A.,Nagi, Mahmoud N.,Habib, El-Sayed E.,Abdel-Aziz, Alaa A.-M.,El-Azab, Adel S.,Abdel-Hamide, Sami G.,Al-Omar, Mohamed A.,Al-Obaid, Abdulrahman M.,El-Subbagh, Hussein I.
experimental part, p. 2849 - 2863 (2010/07/02)
A new series of 2,6-substituted-quinazolin-4-ones was designed, synthesized, and evaluated for their in vitro DHFR inhibition, antimicrobial, and antitumor activities. Compounds 22, 33-37, 39-43, and 45 proved to be active DHFR inhibitors with IC50 range of 0.4-1.0 μM. Compound 18 showed broad-spectrum antimicrobial activity comparable to the known antibiotic gentamicin. Compounds 34 and 36 showed antitumor activity at GI50 (MG-MID) concentrations of 11.2, and 24.2 μM, respectively. Molecular modeling study including flexible alignment; electrostatic, hydrophobic mappings; and pharmacophore prediction were performed. A main featured pharmacophore model was developed which justifies the importance of the main pharmacophoric groups as well as of their relative distances. The substitution pattern and spatial considerations of the π-systems in regard to the quinazoline nucleus proved critical for biological activity.
Thiazolo[5,4-f]quinazolin-9-ones, inhibitors of glycogen synthase kinase-3
Testard, Alexandra,Loge, Cedric,Leger, Benoit,Robert, Jean-Michel,Lozach, Olivier,Blairvacq, Melina,Meijer, Laurent,Thiery, Valerie,Besson, Thierry
, p. 3419 - 3423 (2007/10/03)
In an effort to identify new protein kinase inhibitors with increased potency and selectivity, we have developed the microwave-assisted synthesis of thiazolo[5,4-f]quinazolin-9-ones. The effects of eighteen derivatives on CDK1/cyclin B, CDK5/p25, and GSK-
Efficient synthesis of thiazoloquinazolinone derivatives
Alexandre, Fran?ois-René,Berecibar, Amaya,Wrigglesworth, Roger,Besson, Thierry
, p. 4455 - 4458 (2007/10/03)
An original route to the rare 8H-thiazolo[5,4-f]quinazolin-9-one 1 and the novel 7H-thiazolo[4,5-h]quinazolin-6-one 2 is described. Access to the regioisomers was realized by fusion of a thiazole and a quinazoline ring via Appel's salt chemistry. Thermal
