What are quinazoline derivatives?

What are quinazoline derivatives?

CEP-32496. The quinazoline derivative CEP-32496 is a novel, orally active BRAF inhibitor identified to be highly effective against the proliferation of multiple BRAF(V600E)-dependent cancer cell lines and BRAF(V600E)-dependent xenograft mouse models of human colorectal cancer [82, 83].

What is quinazoline used for?

One of the most important heterocycles in medicinal chemistry are quinazolines possessing wide spectrum of biological properties like antibacterial, antifungal, anticonvulsant, anti-inflammatory, anti-HIV, anticancer and analgesic activities.

Who discovered quinazoline?

The synthesis of quinazoline was first reported in 1895 by August Bischler and Lang through the decarboxylation of the 2-carboxy derivative (quinazoline-2-carboxylic acid).

What is Quinazoline ring?

Quinazoline is a heterocyclic compound of two fused six-membered simple aromatic rings—benzene and pyrimidine ring. It is a yellow-colored compound, found usually in crystalline form.

What are the substitution patterns for quinazoline derivatives?

Synthesis of quinazoline and quinazolinone derivatives substitution patterns of the 1,3-diazine moiety of the system. The first quinazoline reaction of cyanogens with anthranilic acid [15]. Many years later quinazoline was can be synthesized more easily by a different method. From anthranilic acid and formamide. phosphorus trichloride in toluene.

Which is a high yield form of quinazoline?

Oxidation of quinazoline in dilute aqueous acid, with two equivalents of hydrogen peroxide at room temperature gave a high yield of 3,4- dihydro-4-oxo quinazoline. 4 furnished a high yield of 3,4- dihydro-4-oxo quinazoline was also formed.

Where does the alkylation of quinazoline take place?

Alkylation of quinazoline takes place on N, 3- methyl, 3-ethyl-3-alkyl and 3-benzyl quinazolinium salts readily take up a molecule of alcohol to form the corresponding 4-alkoxy-3-alkyl-3,4-dihydro quinazolinium salts.

What are Quinazoline derivatives?

What are Quinazoline derivatives?

CEP-32496. The quinazoline derivative CEP-32496 is a novel, orally active BRAF inhibitor identified to be highly effective against the proliferation of multiple BRAF(V600E)-dependent cancer cell lines and BRAF(V600E)-dependent xenograft mouse models of human colorectal cancer [82, 83].

Which of the following are Quinazoline?

Afatinib

  • Quinazoline-containing drugs.
  • Gefitinib for treatment of non-small-cell lung carcinoma.
  • Lapatinib for treatment of advanced-stage or metastatic breast cancer.
  • Erlotinib, an anti-tumor agent.
  • Afatinib for treatment of cancers resistant to gefinitib and erlotinib.

Is pyrazine a Diazine?

Pyrazine is a diazine that is benzene in which the carbon atoms at positions 1 and 4 have been replaced by nitrogen atoms. It has a role as a Daphnia magna metabolite. It is a member of pyrazines and a diazine. A heterocyclic aromatic organic compounds with the chemical formula C4H4N2.

Why pyrazine is less basic?

Pyridine is a weaker base than saturated amines of similar structure because its electron pair is in an sp2-hybridized orbital, and the electron pair is more tightly held by the atom. Protonation of a similar nitrogen atom in pyrimidine is more favorable because the charge is delocalized to the second nitrogen atom.

Why is pyrimidine more basic than pyrazine?

The pKa of the conjugate acid of pyridine is 5.25. Both N atoms are equivalent and sp2 hybridized. Pyrimidine is less basic than pyridine because of the inductive, electron-withdrawing effect of the second N atom. The pKa of the conjugate acid of pyrimidine is 1.3.

What is pyrimidine synthesis?

Pyrimidine synthesis takes place in cytoplasm. Pyrimidine is synthesized as a free ring and then a ribose-5-phosphate is added to yield direct nucleotides, whereas, in purine synthesis, the ring is made by attaching atoms on ribose-5-phosphate. Pyrimidine atoms come from two sources—carbamoyl phosphate and aspartate.

Is Pyrazine a Diazine?

Pyrazine is a diazine that is benzene in which the carbon atoms at positions 1 and 4 have been replaced by nitrogen atoms. It has a role as a Daphnia magna metabolite. It is a member of pyrazines and a diazine.

What are the starting materials for quinazoline synthesis?

Synthesis of quinazolines. A novel and efficient copper-catalyzed cascade method for the synthesis of quinazolines in good yields uses readily available substituted (2-bromophenyl)methylamines and amidine hydrochlorides as the starting materials, inexpensive CuBr as the catalyst, and economical and environment friendly air as the oxidant.

How is molecular iodine used to make quinazoline?

Molecular iodine catalyses a benzylic sp 3 C-H bond amination of 2-aminobenzaldehydes and 2-aminobenzophenones with benzylamines to provide quinazolines in very good yields.

Which is the correct tandem reaction for quinazoline synthesis?

A mild o -iodoxybenzoic acid (IBX) mediated tandem reaction of readily available o-aminobenzylamine and aldehydes enables a facile synthesis of diversely substituted quinazolines and 3,4-dihydroquinazolines in very good yields. S. Hati, S. Sen, Synthesis, 2016, 48, 1389-1398.

How does singlet diradical Ni ( II ) catalyze the synthesis of quinazoline?

Singlet diradical Ni (II) featuring two antiferromagnetically coupled singlet diradical diamine type ligands catalyzes simple, straightforward, and atom economic syntheses of quinolines, 2-aminoquinolines, and quinazolines in good yields via biomimetic dehydrogenative condensation/coupling reactions.