32658-67-6

Usage

Uses

Used in Pharmaceutical Research:
2-AMINO-5-IODOBENZAMIDE is used as a research compound for the development of new drugs. Its unique structure and reactivity make it a promising candidate for the design and synthesis of novel therapeutic agents. It has been studied for its interactions with biological systems, which can provide insights into its potential pharmacological properties and applications.
Used in Organic Synthesis:
In the field of organic synthesis, 2-AMINO-5-IODOBENZAMIDE serves as a valuable building block for the synthesis of complex organic molecules. Its reactivity and functional groups allow for various chemical transformations, enabling the creation of a wide range of compounds with diverse properties and applications.
Used in Material Science:
2-AMINO-5-IODOBENZAMIDE also finds applications in material science, where it can be used to develop new materials with specific properties. Its unique structure and reactivity can contribute to the design and synthesis of advanced materials for various applications, such as sensors, catalysts, or functional coatings.

InChI:InChI=1/C7H7IN2O/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3H,9H2,(H2,10,11)

Upstream product

• 1397833-74-7 (2-amino-5-iodophenyl) (benzotriazole-1-yl)methanone 
• 20780-76-1 5-iodoisatin 
• 28144-70-9 anthranilic acid amide 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 5326-47-6 2-amino-5-iodobenzoic acid 
• 116027-10-2 5-iodoisatoic anhydride 

Downstream Products

• 929695-95-4 2-(2,4-dihydroxy-phenyl)-6-iodo-3H-quinazolin-4-one 
• 928656-58-0 2-amino-5-(4-pyridinyl)benzamide 
• 16064-08-7 6-iodoquinazolin-4(3H)-one 
• 869299-00-3 ethyl ((2-(aminocarbonyl)-4-iodophenyl)amino)(oxo)acetate 
• 1158963-83-7 N-(2-carbamoyl-4-iodophenyl)furan-2-carboxamide 
• 1417283-64-7 2-benzoyl-6-iodoquinazolin-4(3H)-one 
• 13182-47-3 2-Benzoyl-4(3H)-quinazolinone 
• 1448462-18-7 (E)-2-(3-(3-bromophenyl)acrylamido)-5-iodobenzamide 
• 1448462-19-8 (E)-2-(3-(3-chlorophenyl)acrylamido)-5-iodobenzamide 
• 1448462-20-1 (E)-2-(3-(4-chlorophenyl)acrylamido)-5-iodobenzamide 
• 1448462-25-6 (E)-5-iodo-2-(3-(2-methoxyphenyl)acrylamido)benzamide 
• 1448462-31-4 5-iodo-2-(3-phenylpropiolamido)benzamide 
• 1448462-35-8 5-iodo-2-(3-phenylpropanamido)benzamide 

Relevant academic research and scientific papers

One-pot synthesis ofN-substituted benzannulated triazolesviastable arene diazonium salts

A mild and effective one-pot synthesis of 1,2,3-benzotriazin-4(3H)-ones and benzothiatriazine-1,1(2H)-dioxide analogues has been developed. The method involves the diazotisation and subsequent cyclisation of 2-aminobenzamides and 2-aminobenzenesulfonamidesviastable diazonium salts, prepared using a polymer-supported nitrite reagent andp-tosic acid. The transformation was compatible with a wide range of aryl functional groups and amide/sulfonamide-substituents and was used for the synthesis of pharmaceutically important targets. The synthetic utility of the one-pot diazotisaton-cyclisation process was further demonstrated with the preparation of an α-amino acid containing 1,2,3-benzotriazin-4(3H)-one.

Microwave assisted synthesis and photophysical properties of blue emissive 2-amino-3-carboxamide-1,1′-biaryls and 4-(arylamino)-[1,1′-biphenyl]-3-carboxamides via Suzuki and Chan-Evans-Lam coupling

An efficient microwave assisted synthesis of 2-amino-3-carboxamide-1,1′-biaryls derivatives 4a-p and terphenyl derivative 5a from 2-amino-5-iodobenzamide 2a, 2-amino-3,5-diiodobenzamide 2b and (het)aryl boronic acids via Suzuki coupling has been achieved. Synthetic utility of the product 4-amino-4′-cyano-[1,1′-biphenyl]-3-carboxamide 4j has been demonstrated for the synthesis of 4-(aryl amino)-[1,1′-biphenyl]-3-carboxamide derivatives 10a-c via Chan-Evans-Lam coupling reaction. Furthermore, 4-(4′-oxo-3′, 4′-dihydro-1′H-spiro[fluorene-9,2′-quinazolin]-6′-yl)benzonitrile 12a was obtained from biaryl derivative 4j and fluorenone 11a and 6(4- methoxyphenyl)2-(ferrocenyl) quinazolin-4(3H)-one 12b from biaryl derivative 4k and ferrocenealdehyde 11b using phosphotungstic acid as green catalyst and solvent free microwave irradiation condition. Remarkably, all the synthesized 2-amino-3-carboxamide-1,1′-biaryls and 4-(aryl amino)-[1,1′-biphenyl]-3-carboxamide derivatives 4a-p showed luminescence in the blue region with large Stokes shift. Significantly, 2-amino-3-carboxamide-1,1′-biaryls 4d and 4j showed high fluorescence quantum yields (Φf) 0.54 and 0.84, respectively.

Visible-light induced copper(i)-catalyzed oxidative cyclization of: O -aminobenzamides with methanol and ethanol via HAT

The use of the in situ generated ligand-copper superoxo complex absorbing light energy to activate the alpha C(sp3)-H of MeOH and EtOH via the hydrogen atom transfer (HAT) process for the synthesis of quinazolinones by oxidative cyclization of alcohols with o-aminobenzamide has been investigated. The synthetic utility of this protocol offers an efficient synthesis of a quinazolinone intermediate for erlotinb (anti-cancer agent) and 30 examples were reported.

SUBSTITUTED QUINAZOLINONE DERIVATIVES AND THEIR USE AS POSITIVE ALLOSTERIC MODULATORS OF MGLUR4

The present invention relates to novel quinazolinone derivatives of formula (I) as well as pharmaceutical compositions containing these compounds. The compounds of formula (I) as provided herein can act as positive allosteric modulators of metabotropic glutamate receptor subtype 4 (mGluR4), and can thus be used as therapeutic agents, particularly in the treatment or prevention of conditions associated with altered glutamatergic signalling and/or functions or conditions which can be affected by alteration of glutamate level or signalling.

AN IMPROVED ONE POT, ONE STEP PROCESS FOR THE HALOGENATION OF AROMATICS USING SOLID ACID CATALYSTS

The present invention disclosed an improved one pot, one step process for halogenation of compound of formula (II) to afford corresponding halogenated compound of formula (I) having improved yield and increased selectivity under very mild conditions.

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.

AMINO-ARYL-BENZAMIDE COMPOUNDS AND METHODS OF USE THEREOF

A method for the treatment and/or reduction of nonalcoholic fatty liver disease (NAFLD) and nonalcoholic steatohepatitis (NASH) is disclosed. The method uses active amino-aryl-benzamide compounds and methods for the preparation thereof.

Spectroscopic, DFT, and XRD studies of hydrogen bonds in N-unsubstituted 2-aminobenzamides

The structures of the mono- and the dihalogenated N-unsubstituted 2-aminobenzamides were characterized by means of the spectroscopic (1H-NMR, UV-Vis, FT-IR, and FT-Raman) and X-ray crystallographic techniques complemented with a density functional theory (DFT) method. The hindered rotation of the C(O)-NH2 single bond resulted in non-equivalence of the amide protons and therefore two distinct resonances of different chemical shift values in the 1H-NMR spectra of these compounds were observed. 2-Amino-5-bromobenzamide (ABB) as a model confirmed the presence of strong intramolecular hydrogen bonds between oxygen and the amine hydrogen. However, intramolecular hydrogen bonding between the carbonyl oxygen and the amine protons was not observed in the solution phase due to a rapid exchange of these two protons with the solvent and fast rotation of the Ar-NH2 single bond. XRD also revealed the ability of the amide unit of these compounds to function as a hydrogen bond donor and acceptor simultaneously to form strong intermolecular hydrogen bonding between oxygen of one molecule and the NH moiety of the amine or amide group of the other molecule and between the amine nitrogen and the amide hydrogen of different molecules. DFT calculations using the B3LYP/6-311++G(d,p) basis set revealed that the conformer (A) with oxygen and 2-amine on the same side predominates possibly due to the formation of a six-membered intramolecular ring, which is assisted by hydrogen bonding as observed in the single crystal XRD structure.

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.

NOVEL RECYCLABLE IODINATING AGENT AND ITS APPLICATIONS

The present invention provides a novel recyclable catalysts of formula A, [Formula A should be inserted here] wherein X is selected from the group consisting of [Formula should be inserted here] The present invention also provides a novel recyclable iodinating agent of formula I, II or III and a process for the synthesis thereof. [ Formula I, II & III should be inserted here] Further, the present invention provides a process of halogenation of amines and heterocyclic compounds by employing recyclable catalyst of formula (I).