40545-33-3

Usage

Uses

Used in Pharmaceutical Industry:
2-AMINO-5-METHYLBENZAMIDE is utilized as a building block in the synthesis of various pharmaceuticals, leveraging its chemical properties and structure to contribute to the development of drugs for a range of medical conditions. Its role in drug synthesis is pivotal due to its ability to form the basis of new medicinal compounds.
Used in Organic Chemistry Research:
In the realm of organic chemistry, 2-AMINO-5-METHYLBENZAMIDE serves as a valuable compound for research purposes. Its unique structure allows chemists to explore new reactions and mechanisms, potentially leading to advancements in the synthesis of complex organic molecules and the discovery of novel chemical entities.

InChI:InChI=1/C8H10N2O/c1-5-2-3-7(9)6(4-5)8(10)11/h2-4H,9H2,1H3,(H2,10,11)

Upstream product

• 64113-86-6 2-nitro-5-methylbenzonitrile 
• 4315-12-2 5-methyl-2-nitrobenzamide 
• 4692-99-3 6-methyl-1H-benzo[d][1,3]oxazine-2,4-dione 
• 2941-78-8 2-Amino-5-methylbenzoic acid 
• 620-22-4 3-Methylbenzonitrile 
• 79-37-8 oxalyl dichloride 
• 3113-72-2 5-methyl-2-nitrobenzoic acid 
• 530-62-1 1,1'-carbonyldiimidazole 
• 5925-93-9 2-amino-5-methylbenzonitrile 
• 608-05-9 5-methyl-indole-2,3-dione 
• 38818-49-4 5-methyl-2-nitrobenzoyl chloride 

Downstream Products

• 105189-24-0 6-methyl-2-<3-<3-(1-piperidinylmethyl)phenoxy>propyl>-4(3H)-quinazolinone 
• 112253-74-4 2-azido-5'-methyl-2'-carboxamidobenzanilide 
• 112253-73-3 2-azido-5-bromo-5'-methyl-2'-carboxamidobenzanilide 
• 19181-53-4 6-methyl-3H-quinazolin-4-one 
• 140410-01-1 N-<4-<<(3,4-dihydro-4-oxo-1,2,3-benzotriazin-6-yl)methyl>amino>benzoyl>-L-glutamic acid 
• 140410-03-3 dimethyl N-<4-<<(3,4-dihydro-4-oxo-1,2,3-benzotriazin-6-yl)methyl>amino>benzoyl>-L-glutamate 
• 263713-35-5 2-amino-5-methylbenzylamine 
• 869298-94-2 ethyl ((2-(aminocarbonyl)-4-methylphenyl)amino)(oxo)acetate 
• 1226978-02-4 8-methyl-12-phenyl-5,6-dihydro-4bH-isoquino[2,1-a]quinazolin-6-one 
• 21419-51-2 6-methyl-2-phenylquinazolin-4(3H)-one 
• 1374021-18-7 C₁₇H₁₆N₂O 
• 1403226-79-8 C₁₄H₁₄ClFN₂ 
• 1403226-66-3 N-[[2-[(2-chloro-6-fluorophenyl)amino]-5-methylphenyl]methyl]-1,1,1-trifluoromethanesulfonamide 
• 1403226-70-9 C₁₅H₁₆ClFN₂O₂S 

Relevant academic research and scientific papers

Tunable Electrosynthesis of Anthranilic Acid Derivatives via a C-C Bond Cleavage of Isatins

A facile and direct electrocatalytic C-C bond cleavage/functionalization reaction of isatins was developed. With isatins as the amino-attached C1 sources, a variety of aminobenzoates, and aminobenzamides were synthesized in moderate to good yields under mild conditions.

COMBINATION THERAPY FOR TREATING MPS1

The application is directed to compounds of formula (I) and their salts and solvates, wherein B, R1, R2, R3, R3', R4, R4', and R5 are as set forth in the specification, as well as to methods for their preparation, pharmaceutical compositions comprising the same, and use thereof for the treatment and/or prevention of, e.g., MPS1, optionally in combination with α-L-iduronidase or an analog or variant thereof, e.g., laronidase.

Oxidative ring-opening of isatins for the synthesis of 2-aminobenzamides and 2-aminobenzoates

An efficient and practical isatin-based oxidative domino protocol has been developed for the facile synthesis of 2-aminobenzamides and 2-aminobenzoates. The robust nature of this reaction system is reflected by accessible starting materials, room temperature and high-yield gram-scale synthesis.

Trash to treasure: Eco-friendly and practical synthesis of amides by nitriles hydrolysis in WepPA

The hydration of nitriles to amides in a water extract of pomelo peel ash (WEPPA) was realized with moderate to excellent yields without using external transition metals, bases or organic solvents. This reaction features a broad substrate scope, wide functional group tolerance, prominent chemoselectivity, and good reusability. Notably, a magnification experiment in this bio-based solvent at 100 mmol further demonstrated its practicability.

POLY-ADP RIBOSE POLYMERASE (PARP) INHIBITORS

The present invention is related to a pharmaceutical composition comprising a pharmaceutically acceptable carrier or diluent and a compound represented by the following structural formula: The present invention is also related a method of treating a subject with a disease which can be ameliorated by inhibition of poly(ADP-ribose)polymerase (PARP). The definitions of the variables are provided herein.

Anthranilamide-based 2-phenylcyclopropane-1-carboxamides, 1,1'-biphenyl-4-carboxamides and 1,1'-biphenyl-2-carboxamides: Synthesis biological evaluation and mechanism of action

Several anthranilamide-based 2-phenylcyclopropane-1-carboxamides 13a-f, 1,1’-biphenyl-4-carboxamides 14a-f and 1,1’-biphenyl-2-carboxamides 17a-f were obtained by a multistep procedure starting from the (1S,2S)-2-phenylcyclopropane-1-carbonyl chloride 11, the 1,1'-biphenyl-4-carbonyl chloride 12 or the 1,1'-biphenyl-2-carbonyl chloride 16 with the appropriate anthranilamide derivative 10a-f. Derivatives 13a-f, 14a-f and 17a-f showed antiproliferative activity against human leukemia K562?cells. Among these derivatives 13b, 14b and 17b exerted a particular cytotoxic effect on tumor cells. Derivative 17b showed a better antitumoral effect on K562?cells than 13b and 14b. Analyses performed to explore 17b mode of action revealed that it induced an arrest in G2/M phase of cell cycle which was consequent to DNA lesions as demonstrated by the increase in phospho-ATM and γH2AX, two known markers of DNA repair response system. The effect of 17b was also related to ROS generation, activation of JNK and induction of caspase-3 dependent apoptosis.

One-Pot Cascade Synthesis of Quinazolin-4(3H)-ones via Nickel-Catalyzed Dehydrogenative Coupling of o-Aminobenzamides with Alcohols

In this paper, we report a general, efficient, and environmentally benign method for the one-pot cascade synthesis of quinazolin-4(3H)-ones via acceptorless dehydrogenative coupling of o-aminobenzamide with alcohols catalyzed by a simple Ni(II) catalyst, [Ni(MeTAA)], featuring a tetraaza macrocyclic ligand (tetramethyltetraaza[14]annulene (MeTAA)). A wide variety of substituted quinazolin-4(3H)-ones were synthesized in high yields starting from readily available benzyl alcohols and o-aminobenzamides. Several controlled reactions along with deuterium labeling studies were carried out to establish the acceptorless dehydrogenative nature of the reactions.

On the Synthesis and Reactivity of 2,3-Dihydropyrrolo[1,2- a ]quinazolin-5(1 H)-ones

An improved, scalable synthetic route to the quinazolinone natural product 2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-one is reported. The applicability of this method to analogue synthesis and the synthesis of related natural products is explored. Finally, reactivity of the scaffold to a variety of electrophilic reagents, generating products stereoselectively, is reported.

Structure-activity relationships of 2-arylquinazolin-4-ones as highly selective and potent inhibitors of the tankyrases

Tankyrases (TNKSs), members of the PARP (Poly(ADP-ribose)polymerases) superfamily of enzymes, have gained interest as therapeutic drug targets, especially as they are involved in the regulation of Wnt signalling. A series of 2-arylquinazolin-4-ones with varying substituents at the 8-position was synthesised. An 8-methyl group (compared to 8-H, 8-OMe, 8-OH), together with a 4′-hydrophobic or electron-withdrawing group, provided the most potency and selectivity towards TNKSs. Co-crystal structures of selected compounds with TNKS-2 revealed that the protein around the 8-position is more hydrophobic in TNKS-2 compared to PARP-1/2, rationalising the selectivity. The NAD+-binding site contains a hydrophobic cavity which accommodates the 2-aryl group; in TNKS-2, this has a tunnel to the exterior but the cavity is closed in PARP-1. 8-Methyl-2-(4-trifluoromethylphenyl)quinazolin-4-one was identified as a potent and selective inhibitor of TNKSs and Wnt signalling. This compound and analogues could serve as molecular probes to study proliferative signalling and for development of inhibitors of TNKSs as drugs.

Synthesis, antiproliferative activity and possible mechanism of action of novel 2-acetamidobenzamides bearing the 2-phenoxy functionality

Several new 2-(2-phenoxyacetamido)benzamides 17a-v, 21 and 22 were synthesized by stirring in pyridine the acid chlorides 16a-e and the appropriate5-R-4-R1-2-aminobenzamide 15a-e and initially evaluated in vitro for antiproliferative activity against the K562 (human chronic myelogenous leukemia) cell line. Some of synthesized compounds were evaluated for their in vitro antiproliferative activity against the full NCI tumor cell line panel derived from nine clinically isolated cancer types (leukemia, non-small cell lung, colon, CNS, melanoma, ovarian, renal, prostate and breast). The most active compounds caused an arrest of K562 cells in the G0-G1 phase of cell cycle and induction of apoptosis, which was mediated by caspase activation.