57097-71-9

Upstream product

• 610-14-0 2-nitrobenzyl chloride 
• 140472-37-3 N-(o-nitrobenzoyl)-phtalimide 
• 136918-14-4 phthalimide 
• 140472-44-2 2-(4-Hydroxy-1,2-dihydro-quinazolin-2-yl)-benzoic acid 
• 201230-82-2 carbon monoxide 
• 28144-70-9 anthranilic acid amide 
• 6630-33-7 ortho-bromobenzaldehyde 
• 119-67-5 o-carboxybenzaldehyde 

Relevant academic research and scientific papers

A Catalyst-Free One-Pot Protocol for the Construction of Substituted Isoindolinones under Sustainable Conditions

An operationally simple, one-pot, catalyst-free method was developed for the synthesis of pharmaceutically important substituted isoindolinones by a three-component reaction of 2-formylbenzoic acid, a primary amine, and a 1,3-dione in ethanol under dielectric heating.

Development of dual inhibitors targeting pyruvate dehydrogenase kinases and human lactate dehydrogenase A: High-throughput virtual screening, synthesis and biological validation

Most cancer cells feature an altered glucose metabolism from oxidative phosphorylation to cytoplasmic glycolysis. Pyruvate dehydrogenase kinases (PDKs) and lactate dehydrogenase A (LDHA) play crucial roles in promotion of glycolysis, thus the inhibition of both enzymes is considered a promising strategy for developing of anticancer therapeutics. Herein, we describe the first discovery of series novel dual inhibitors targeting PDKs and LDHA. We identified 6 hits from a library database containing 485465 compounds through a high-throughput virtual screening assay. Hit-to-lead optimization enabled us to discover two compounds, namely 20e and 20k, which inhibited PDKs with IC50 values of 0.8, and 1.6 μM, respectively, and inhibited LDHA with IC50 values of 0.15 and 0.7 μM, respectively. Meanwhile, the two compounds reduced A549 cell proliferation with EC50 values of 13.2, and 15.7 μM. Furthermore, 20e and 20k decreased the lactate formation, and increased oxygen consumption, suggesting the two compounds modulated the glucose metabolic pathways in cancer cells.

Synthesis of new quinazoline-containing hydroxamic acids as potential HDAC/VEGFR inhibitors. Unusual rearrangements with pyrrolidone ring opening and dehydration of 3-N-hydroxyquinazoline fragment containing tetracycles

Synthesis pathways were developed and new hydroxamic acids were obtained as potential inhibitors of HDAC/VEGFR2, including tetracycles containing quinazolinone fragment as a “cap”. Further biological testing of the obtained compounds will give an opportunity to estimate the real prospects of the chosen research direction.

Trifluoroethanol and liquid-assisted grinding method: a green catalytic access for multicomponent synthesis

An efficient and versatile mechanochemical route for the synthesis of chromene and isoindolo[2,1-a]quinazoline scaffolds has been developed via a simple mortar and pestle liquid-assisted grinding method using 2,2,2-trifluoroethanol (TFE) as an efficient catalyst. The present protocol is very efficient as it offers reaction in mild reaction condition, cleaner reaction profiles, effortless work-up step with excellent purity, and high yield of the desired products with short reaction time.

One-pot three-component selective synthesis of isoindolo[2,1-: A] quinazoline derivatives via a palladium-catalyzed cascade cyclocondensation/cyclocarbonylation sequence

A practical and highly efficient procedure for the selective preparation of 6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-diones through a palladium-catalyzed one-pot three-component cascade reaction of 2-aminobenzamides with 2-bromobenzaldehydes and carbon monoxide under atmospheric pressure has been developed. This cascade reaction, in which four new C-C/C-N bonds and two new rings are simultaneously constructed, is triggered by a cyclocondensation of 2-aminobenzamides with 2-bromobenzaldehydes, followed by a Pd-catalyzed cyclocarbonylation of the in situ formed 2,3-dihydroquinazolin-4(1H)-ones with CO (1 atm). Compared with the existing methods, the present protocol has the advantages of readily available starting materials, broad substrate scope, structural diversity of products, and free of high-pressure equipment.

Method for synthesizing 6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-dione compounds

The invention discloses a method for synthesizing 6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-dione compounds, and belongs to the technical field of organic synthesis. The target products 6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-dione compounds are prepared through a heating and stirring reaction on initial raw materials comprising anthranilamide compounds, o-bromobenzaldehyde compounds and CO in an organic solvent at 120 DEG C under the action of a catalyst, a ligand and an alkali. The method has the advantages of easily available initial raw materials, wide application range of a substrate, high regioselectivity and no high-pressure devices.

Synthesis of Isoindolo[2,1-a]quinazoline, Isoindolo[2,1-a]pyrrolo [2,1-c]quinoxalinone, and Indolo[1,2-a]isoindolo[1,2-c]quinoxalinone Derivatives in a Deep Eutectic Solvent

2-Formylbenzoic acid reacts with various derivatives of 2-aminobenzamide, 2-(1H-pyrrol-1-yl)aniline or 2-(1H-indol-1-yl)aniline in a deep eutectic solvent to give the corresponding derivatives of 6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-dione, isoindolo[2,1-a]pyrrolo[2,1-c]quinoxalin-10(14bH)-one, and indolo[1,2-a]isoindolo[1,2-c]quinoxalin-11(15bH)-one, respectively . This protocol is operationally simple, mild, and efficient.

Isoindolo[2, 1-A]quinazoline derivatives for stabilization of organic materials

The present invention relates to a composition, which comprises a) an organic material susceptible to oxidative, thermal or light-induced degradation, which is a polymer, an oligohydroxy compound, a wax, a fat or a mineral oil, with the proviso that the polymer is not a polypeptide, agar-agar or a component of agar-agar and the oligohydroxy compound is not glucose or a component of agar-agar; and b) a compound of formula (I) n is 1, 2, 3 or 4; when n is 1, R5 is H, C1-C30-alkyl, C3-C10-cycloalkyl, C6-C10-aryl, which is unsubstituted or substituted by C1-C8-alkyl, C1-C8-alkoxy, halogen or one phenyl, C7-C13-aralkyl, C2-C22-alkenyl, C3-C12-alkinyl, OH, C1-C30-alkyloxy, C3-C10-cycloalkyloxy, C6-C12-aryloxy, C7-C13-aralkyloxy, hydroxy-C1-C8-alkyl, carboxy-C1-C12-alkyl, C1-C12-alkoxycarbonyl-C1-C12-alkyl, C2-C30-alkyl, which is interrupted by one or more oxygen atoms, C2-C16-alkyl, which is interrupted by one sulfur atom, or NR′1R′2; when n is 2, R5 is C1-C12-alkane-diyl, C6-C14-arylene, C4-C8-cycloalkane-bis-(C1-C4-alkylene), C6-C14-arene-bis-(C1-C4-alkylene), C4-C24-alkane-diyl, which is interrupted by one or more oxygen atoms, C4-C20-alkane-diyl, which is interrupted by one or more —NH—, —N(C1-C8-alkyl)- or —N(hydroxy-C1-C8-alkyl)-, piperazine-N,N′-bis-(C1-C4-alkylene) or C2-C10-alkane-diyl, which is interrupted by one sulfur atom; R1 to R4 and R6 to R9 are each independently from each other H, C1-C12-alkyl, C3-C10-cycloalkyl, C3-C22-alkenyl, C1-C12-alkoxy, C1-C12-alkylsulfanyl, hydroxy- C1-C8-alkyl, halogen, NR″1R″2, NO2, CN, phenyl, phenyloxy or R1 and R2 or R2 and R3 or R3 and R4 or R6 and R7 or R7 and R8 or R8 and R9 are linked together to form a five- or 6-membered alicylic, aromatic or heterocyclic ring together with their 2 corresponding carbons atoms, to which they are attached.

Synthesis of isoindolo[2,1-a]quinazoline derivatives in ionic liquid catalyzed by iodine

A mild, green, and facile method for the synthesis of 6,6a- dihydroisoindolo[2,1-a]quinazoline-5,11-dione derivatives is described in high yields using ionic liquids as green media. The method involves the reaction of 2-aminobenzamides with 2-formylbenzoic acid catalyzed by iodine and provides a new alkaloid library with potential activity for biomedical screening.

Substituted 2-formylbenzoic acids in the synthesis of 11H-isoindolo[2,1-a] benzimidazol-11-ones, 5H-isoindolo[2,1-a][3,1]benzoxazine-5,11(6aH)-diones, and 6,6a-dihydroisoindolo-[2,1-a]quinazoline-5,11-diones

Optimal conditions were developed for the synthesis of 11H-isoindolo[2,1-a] benzimidazol-11-one, 5H-isoindolo[2,1-a][3,1]benzoxazine-5,11(6aH)-dione, and 6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-dione derivatives in the reaction of substituted 2-formylbenzoic acids with o-phenylenediamine, anthranilic acid, and anthranilamide, respectively. The bifolded structure of 6,6a- dihydroisoindolo-[1,2-a]quinazoline-5,11-dione was verified and investigated.