28461-49-6

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-5-methylbenzene-1-carbohydrazide is used as a reagent in the synthesis of pharmaceuticals for its ability to form coordination complexes with metal ions, which can enhance the properties and efficacy of certain drugs.
Used in Dye Industry:
In the dye industry, 2-Amino-5-methylbenzene-1-carbohydrazide is used as a reagent in the preparation of dyes, contributing to the development of new colorants and improving the performance of existing ones.
Used in Corrosion Inhibition:
2-Amino-5-methylbenzene-1-carbohydrazide is used as a corrosion inhibitor, leveraging its chelating properties to form complexes with metal ions and protect materials from corrosion.
Used in Pyrazole Synthesis:
In the pharmaceutical industry, 2-Amino-5-methylbenzene-1-carbohydrazide is used as a precursor in the synthesis of pyrazole, a compound with applications in the development of various drugs.

InChI:InChI=1/C8H11N3O/c1-5-2-3-7(9)6(4-5)8(12)11-10/h2-4H,9-10H2,1H3,(H,11,12)

Upstream product

• 4692-99-3 6-methyl-1H-benzo[d][1,3]oxazine-2,4-dione 
• 18595-16-9 2-amino-5-methylbenzoic acid methyl ester 
• 2941-78-8 2-Amino-5-methylbenzoic acid 

Downstream Products

• 96134-67-7 4-Methyl-2-(5-methyl-1,3,4-oxadiazol-2-yl)benzeneamine 
• 85516-74-1 dimethyl-2,7 dihydro-3,4 benzotriazepine-1,3,4 (5H) one-5 
• 85516-81-0 amino-3 dimethyl-2,6 (3H) quinazolinone-4 
• 1403672-19-4 C₁₄H₁₃N₅ 
• 1403672-15-0 2-(9-methyl-2-pyridin-2-yl-5,6-dihydro[1,5-c]quinazolin-5-yl)phenol 
• 1427683-42-8 2-amino-N′-(imidazolidin-2-ylidene)-5-methylbenzohydrazide 
• 96498-99-6 7-Methyl-2-phenyl-3,4-dihydro-5H-1,3,4-benzotriazepin-5-one 
• 96499-02-4 2-(2-Amino-5-methylphenyl)-5-phenyl-1,3,4-oxadiazole 
• 93595-55-2 5-(2-Amino-5-methyl-phenyl)-3H-[1,3,4]oxadiazol-2-one 
• 773143-40-1 5-(2-amino-5-methyl-phenyl)-3H-[1,3,4]oxadiazole-2-thione 

Relevant academic research and scientific papers

Discovery of phthalazino[1,2-b]-quinazolinone derivatives as multi-target HDAC inhibitors for the treatment of hepatocellular carcinoma via activating the p53 signal pathway

In view of histone deacetylases (HDACs) as a promising target for cancer therapy, a series of phthalazino[1,2-b]-quinazolinone units were hybrided with ortho-aminoanilide or hydroxamic acid to serve as multi-target HDAC inhibitors for the treatment of solid tumors. Among the target compounds, 8h possessed nano-molar IC50 values toward the tested cancer cells and HDAC subtypes, which was more potent than the HDAC inhibitor SAHA (vorinostat). Mechanism study revealed that compound 8h could suppress the HepG2 cell proliferation via prompting the acetylation of histone 3 (H3) and α-tubulin, and activating the p53 signal pathway as designed. In addition, compound 8h exhibited much stronger in vivo antitumor efficacy than SAHA in the HepG2 xenograft tumor model with negligible toxicity. As a novel multi-target HDAC inhibitor, compound 8h deserves further development as a potential anticancer agent.

Phthalazino[1,2-b]quinazolinones as p53 Activators: Cell Cycle Arrest, Apoptotic Response and Bak-Bcl-xl Complex Reorganization in Bladder Cancer Cells

p53 inactivation is a clinically defined characteristic for cancer treatment-nonresponsiveness. It is therefore highly desirable to develop anticancer agents by restoring p53 function.1 Herein the synthesized phthalazino[1,2-b]quinazolinones were discovered as p53 activators in bladder cancer cells. 10-Bromo-5-(2-dimethylamino-ethylamino)phthalazino[1,2-b]quinazolin-8-one (5da) was identified as the most promising candidate in view of both its anticancer activity and mechanisms of action. 5da exhibited strong anticancer activity on a broad range of cancer cell lines and significantly reduced tumor growth in xenograft models at doses as low as 6 mg/kg. Furthermore, 5da caused cell cycle arrest at S/G2 phase, induced apoptosis, changed cell size, and led to cell death by increasing the proportion of sub-G1 cells. Molecular mechanism studies suggested that accumulation of phospho-p53 in mitochondria after 5da treatment resulted in conformational activation of Bak, thereby evoking cell apoptosis, finally leading to irreversible cancer cell inhibition. Our present studies furnish new insights into the molecular interactions and anticancer mechanisms of phospho-p53-dependent quinazolinone compound.

A diversity oriented synthesis of 2,10-dioxo-10H-1,2,3,4,4a,5-hexahydropyridazino[3,2-b]quinazolines

A parallel method for the synthesis of the title compounds is described. Thus, methyl anthranilates (5) are transformed into 2-aminobenzohydrazides (3) which were treated with 4-oxo acids (4) to afford in high yields and acceptable purity of piridazino[3,2-b]quinazolines (1). Compounds (1) present four diversity centers (R1, R2, R3, and R4). The range of chemically acceptable substituents at each center has been evaluated. The isolation of a possible intermediate in the formation of 1, which presents an amino structure (10), has allowed proposing a complete mechanistic rationalization for the formation of structures (1).

Synthesis and Pharmacological Evaluation of Fenamate Analogues: 1,3,4-Oxadiazol-2-ones and 1,3,4-Oxadiazole-2-thiones

A series of fenamate pyridyl or quinolinyl analogues of 1,3,4-oxadiazol-2-ones 5a-d and 6a-r, and 1,3,4-oxadiazole-2-thiones 5e-g and 6s-v, respectively, have been synthesized and evaluated for their analgesic (hot-plate), antiinflammatory (carrageenin induced rat's paw edema) and ulcerogenic effects as well as plasma prostaglandin E2 (PGE 2) level. The highest analgesic activity was achieved with compound 5a (0.5, 0.6, 0.7 mmol/kg b.wt.) in respect with mefenamic acid (0.4 mmol/kg b.wt.). Compounds 6h, 61 and 5g showed 93, 88 and 84% inhibition, respectively on the carrageenan-induced rat's paw edema at dose level of 0.1mmol/kg, b.wt, compared with 58% inhibition of mefenamic acid (0.2mmol/kg b.wt.). Moreover, the highest inhibitory activity on plasma PGE2 level was displayed also with 6h, 61 and 5g (71, 70, 68.5% respectively, 0.1mmol/kg b.wt.) compared with indomethacin (60%, 0.01 mmol/kg b.wt.) as a reference drug. In addition 6i, 6k, 6p, 6r, 6t and 6v were devoid of any ulcerogenicity.

The Chemistry of 2-Aminobenzoyl Hydrazides. 1. Effects of Orthoester Substituents on the Mode of Cyclization

Treatment of substituted 2-aminobenzoyl hydrazides with orthoesters has been found to yield different products depending upon the type of orthoester employed.Equimolar quantities of orthoester and hydrazide yield 3-amino-4(3H)-quinazolinones, whereas utilization of a two-fold excess (or greater) of orthoester yields, in some cases, 3,4-dihydro-5H-1,3,4-benzotriazepin-5-ones as minor products in addition to N-imidate esters as major products.Treatment of hydrazides with trimethyl orthobenzoate yields substituted 5-(2-aminophenyl)-1,3,4-oxadiazoles and 3,4-dihydro-5H-1,3,4-benzotriazepin-5-ones.The steric bulk of the phenyl group in trimethyl orthobenzoate effects the formation of adduct at the β-nitrogen of the hydrazide which cyclized to the oxadiazole and benzotriazepinone products.In the aliphatic orthoester series, the formation of adduct to the aromatic amino group appears to be favored which gives rise to quinazolinone and benzotriazepinone products.

Pyrazoloquinazolin-9-ones: A New Series of Antiallergic Agents

A new series of antiallergic agents, pyrazoloquinazolin-9-ones, was synthesized and evaluated for inhibitory effects in the rat reaginic passive cutaneous anaphylaxis (PCA) screen.Several analogues were found to be more potent than cromolyn sodium intravenously.Structure-activity relationships are discussed.One of the compounds, 4,9-dihydro-5-methoxy-9-oxopyrazoloquinazoline-2-carboxylic acid (36), was found to be approximately 250 times more potent than cromolyn sodium intravenously.