34425-87-1

Usage

Functional Groups

Chlorobenzoyl group: This group consists of a benzene ring with a chlorine atom attached directly to the benzene ring and connected to the rest of the molecule via a carbonyl group (C=O).
Amino group: This group consists of a nitrogen atom bonded to two hydrogen atoms and connected to the rest of the molecule via a carbonyl group.

Applications

Building block in pharmaceutical synthesis
Building block in agrochemical synthesis
Research reagent in organic chemistry and biochemistry studies

Potential Applications

Development of new drugs
Development of crop protection products

Chemical Properties

Due to its unique structure, 2-[(4-chlorobenzoyl)amino]benzoic acid exhibits specific chemical reactivity that makes it valuable in various synthetic pathways for pharmaceuticals and agrochemicals.

InChI:InChI=1/C14H10ClNO3/c15-10-7-5-9(6-8-10)13(17)16-12-4-2-1-3-11(12)14(18)19/h1-8H,(H,16,17)(H,18,19)

Upstream product

• 122-01-0 4-chloro-benzoyl chloride 
• 118-92-3 anthranilic acid 
• 18600-52-7 2-(4-chlorophenyl)-4H-benzo[d][1,3]oxazin-4-one 
• 134-20-3 2-carbomethoxyaniline 
• 37619-18-4 methyl 2-(4-chlorobenzamido)benzoate 
• 108-88-3 toluene 
• 1211-35-4 2-(4-chlorophenyl)-1H-indole 
• 74-11-3 para-chlorobenzoic acid 

Downstream Products

• 1314602-98-6 C₂₂H₁₇ClN₄O₄S 
• 1314603-07-0 4-amino-N-[2-(4-chlorophenyl)-4-oxoquinazolin-3(4H)-yl]benzenesulfonamide 
• 104830-73-1 4-chloro-N-(2-hydrazinocarbonyl-phenyl)benzamide 
• 18600-52-7 2-(4-chlorophenyl)-4H-benzo[d][1,3]oxazin-4-one 

Relevant academic research and scientific papers

A straightforward TBHP-mediated synthesis of 2-amidobenzoic acids from 2-arylindoles and their antimicrobial activity

A simple and highly efficient strategy has been developed for the synthesis of 2-amidobenzoic acids through the tert-butyl hydroperoxide (TBHP)-mediated oxygenation and sequential ring opening of 2-arylindoles in a one-pot fashion under metal-free aerobic conditions. The developed synthetic protocol is operationally simple, tolerates a wide range of functional groups, and is amenable to the gram-scale. Radical trapping experiments revealed that the reaction involves a radical pathway. The synthesized compounds (2a-s) were tested for in vitro antimicrobial activity. Among all screened compounds, 2d showed the maximum antibacterial activity against P. aerugunosa (ZOI = 17 mm, MIC = 32 μg mL-1) and compounds 2d and 2p showed the maximum (32 μg mL-1) antifungal activity against A. flavus and C. albicans.

Radical-Induced, Palladium-Catalyzed C–H Activation: An Approach to Functionalize 4H-Benzo[d][1,3]oxazin-4-one Derivatives by Using Toluenes, Aldehydes, and Benzyl Alcohols

Toluenes, aldehydes, and benzyl alcohols have been utilized in the radical-induced direct functionalization of 4H-benzo[d][1,3]oxazin-4-one derivatives by using a palladium-catalyzed C–H activation strategy. The stability, low toxicity, and ease of access

Substituent effects on hydrogen bonding of aromatic amide-carboxylate

N-(p-benzoyl)-anthranilic acid (BAA) derivatives have been synthesized with different substituents (X: Br, Cl, OCH3, CH3), and their crystal structures have been analyzed in order to understand the variations in their molecular geome

Synthesis, antiphospholipase A2, antiprotease, antibacterial evaluation and molecular docking analysis of certain novel hydrazones

Some novel hydrazone derivatives 6a-o were synthesized from the key intermediate 4-Chloro-N-(2-hydrazinocarbonyl-phenyl)-benzamide 5 and characterized using IR, 1H-NMR, 13C-NMR, mass spectroscopy and elemental analysis. The inhibitor

Benzenesulfonamides incorporating bulky aromatic/heterocyclic tails with potent carbonic anhydrase inhibitory activity

Three series of sulfonamides incorporating long, bulky tails were obtained by applying synthetic strategies in which substituted anthranilic acids, quinazolines and aromatic sulfonamides have been used as starting materials. They incorporate long, bulky diamide-, 4-oxoquinazoline-3-yl- or quinazoline-4-yl moieties in their molecules, and were investigated for the inhibition of four physiologically relevant carbonic anhydrase (CA, EC 4.2.1.1) isoforms, the cytosolic human (h) hCA I and II, as well as the transmembrane hCA IX and XII. Most of the new sulfonamides showed excellent inhibitory effects against the four isoforms, with KIs of 7.6-322 nM against hCA I, of 0.06-85.4 nM against hCA II; of 6.7-152 nM against hCA IX and of 0.49-237 nM against hCA XII; respectively. However no relevant isoform-selective behavior has been observed for any of them, although hCA II and XII, isoforms involved in glaucoma-genesis were the most inhibited ones. The structure-activity relationship for inhibiting the four CAs with these derivatives is discussed in detail.

Precursor-directed combinatorial biosynthesis of cinnamoyl, dihydrocinnamoyl, and benzoyl anthranilates in saccharomyces cerevisiae

Biological synthesis of pharmaceuticals and biochemicals offers an environmentally friendly alternative to conventional chemical synthesis. These alternative methods require the design of metabolic pathways and the identification of enzymes exhibiting ade

Substituent effects on energetics of peptide-carboxylate hydrogen bonds as studied by 1H NMR spectroscopy: Implications for enzyme catalysis

Substituent effects in N-H···O hydrogen bonds were estimated by comparing the acidities of two series of model compounds: N-benzoylanthranilic acids (A) and 4-benzoylamidobenzoic acids (B). Intramolecular N-H···O hydrogen bonds were found to be present in the A series of compounds, while B acids were used as control models. The respective pKa values for A and B acids were determined experimentally in DMSO solution using proton NMR spectroscopy. With X = H, the pKa for A and B acids were observed to be 7.6 and 11.6, respectively, a difference of 4.0 units (ΔpKa). However, with X = p-NO 2, the ΔpKa value between A and B acids increased to 4.7 units: the pKa values for A and B acids were determined as 6.7 and 11.4, respectively. The ΔpKa values between A and B acids as a function of the X substituents were studied in 10 other examples. The effects of X substituents in A acids could be predicted on the basis of the observed linear Hammett correlations, and the sensitivity of each substituent effect was found to be comparable to those observed for the ionization of substituted benzoic acids (ρ = 1.04 for A acids, and ρ = 1.00 for benzoic acids).

Synthesis of some new glutamine linked 2,3-disubstituted quinazolinone derivatives as potent antimicrobial and antioxidant agents

A series of novel glutamine linked 2,3-disubstituted quinazolinone conjugates was synthesized from methyl anthranilate and different substituted acids and acid chlorides. The compounds 5a-l were prepared in good yields. All compounds were screened for their antibacterial activity against Gram-positive and Gram-negative bacteria and for antifungal activity against Candida albicans and Aspergillus flavus using paper disk diffusion technique. The minimum inhibitory concentrations of the compounds were also determined by agar streak dilution method. The compound 5b was found to exhibit the most potent in vitro anti-microbial activity. When tested for their antioxidant activity, compounds 5i and 5l showed potent radical scavenging activity, while compound 5g had moderate effect against 2,2-diphenyl-1-picrylhydrazyl, hydroxyl, nitric oxide, and superoxide radical scavenging assays. These results suggest that, the three quinazolinone analogs (5g, 5i, and 5l) could be considered as useful templates for future development to obtain more potent antioxidant agents.

Synthesis, analgesic and anti-inflammatory evaluation of some novel quinazoline derivatives

Two series of some new 2,4,6-trisubstituted-quinazoline derivatives were prepared and screened for their analgesic, anti-inflammatory activity and acute toxicity. Four compounds were more potent analgesic agents than the reference drug Indomethacin and thirteen compounds showed significant anti-inflammatory activity. Seven compounds showed combined ability to inhibit both pain and inflammation. Compounds tested for acute toxicity showed no toxic symptoms or mortality rates 24 h post-administration implying their good safety margin.

A new synthesis of 2-substituted 4H-3,1-benzoxazin-4-ones by cyanuric chloride cyclodehydration of N-benzoyl- and N-acylanthranilic acids

A new and a convenient method for the synthesis of aryl- and alkyl-2-substituted 4H-3,1-benzoxazin-4-ones by cyclodehydration of N-benzoyl- and N-acylanthranilic acid by cyanuric chloride is described.