6828-35-9

Usage

Chemical Properties

White solid

InChI:InChI=1/C6H5ClIN/c7-4-1-2-5(8)6(9)3-4/h1-3H,9H2

Upstream product

• 5446-05-9 4-chloro-2-nitroiodobenzene 
• 108-42-9 3-chloro-aniline 
• 89-63-4 4-Chloro-2-nitroaniline 
• 6781-33-5 5-chloro-2-iodoaniline hydrochloride 
• 142-71-2 copper diacetate 
• 64-19-7 acetic acid 

Downstream Products

• 136808-72-5 2-iodo-5-chlorophenol 
• 153042-33-2 tert-butyl (5-chloro-2-iodophenyl)carbamate 
• 1006-99-1 2-methyl-5-chloro-benzothiazole 
• 20358-00-3 2-amino-5-chlorobenzothiazole 
• 274926-23-7 (5-chloro-2-iodo-phenyl)-(4-methoxybenzyl)-amine 
• 960608-47-3 5-chloro-2-(phenylethynyl) aniline 
• 252349-70-5 (R)-2-(5-Chloro-2-iodo-phenylamino)-4-oxo-butyric acid (R)-1-isobutoxycarbonyl-ethyl ester 
• 476689-66-4 tert-butyl-(2R)-2-({(2E)-2-[(5-chloro-2-iodophenyl)imino]ethanoyl}oxy)propanoate 
• 150869-42-4 methyl trans-4-chloro-2-aminocinnamate 
• 827325-71-3 3-{2-[3-(3-bromophenyl)ureido]-4-chlorophenyl}propionic acid methyl ester 
• 33468-35-8 6-chloro-DL-tryptophan 
• 274926-24-8 N-(5-chloro-2-iodo-phenyl)-N-(4-methoxybenzyl)-malonamic acid methyl ester 
• 274926-25-9 N-(5-chloro-2-iodo-phenyl)-N-(4-methoxybenzyl)-malonamic acid 
• 274926-28-2 (E)-8-chloro-1-(4-methoxybenzyl)-2-oxo-5-phenylcarbamoylmethylene-2,3,4,5-tetrahydro-1H-benzo[b]azepine-3-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Au-catalyzed formation of functionalized quinolines from 2-alkynyl arylazide derivatives

A new method for converting 2-alkynyl arylazide derivatives into functionalized polysubstituted quinolines following a gold-catalyzed 1,3-acetoxy shift/cyclization/1,2-group shift sequence has been developed. This transformation proceeds under mild reaction conditions, is efficient, and tolerates a large variety of functional groups.

Synthesis and structural insights of substituted 2-iodoacetanilides and 2-iodoanilines

This study reports a simple and efficient method for the direct iodination of substituted anilines with molecular iodine and copper acetate in acetic acid producing 2-iodoacetanilies and 2-iodoanilines. Employing density functional theory (B3LYP) and MidiX basis set, computational study is performed to calculate equilibrium geometries, IR vibrational frequencies, and thermodynamic properties including change of energy, enthalpy and Gibbs free energies. The optimized geometries indicated longer C-I bond distance (2.133 ?) which makes iodine slightly positive. The partial atomic charge profile and electrostatic potential further confirmed that most of the iodinated products are capable of forming a distinct halogen bonding . The thermodynamic properties disclosed that all iodination reactions are endothermic. Understanding the substituents' effect, molecular frontier orbital (MO) calculations are conducted finding the HOMO, LUMO and HOMO-LUMO gaps for all compounds. The MO calculations revealed that two electron-withdrawing iodine groups have significant influence on lowering the HOMO-LUMO gap compared to one iodine group in the products.

Remarkable switch in the regiochemistry of the iodination of anilines by N-iodosuccinimide: Synthesis of 1,2-dichloro-3,4-diiodobenzene

Direct iodination of anilines by NIS in polar solvents (such as DMSO) affords p-iodinated products with up to >99% regioselectivity. Switching to less polar solvents (such as benzene) in the presence of AcOH inverts this outcome toward dramatically increased or preferential generation of the o-isomers, also with up to >99% regioselectivity. This finding was exploited in the synthesis of 1,2-dichloro-3,4-diiodobenzene. Georg Thieme Verlag Stuttgart - New York.

Total synthesis of chloptosin: A dimeric cyclohexapeptide

Here we describe in full our investigations into the synthesis of the dimeric cyclohexapeptide chloptosin in 17 linear steps. Particularly, this work features an organocatalytic tandem process for the synthesis of the embedded piperazic acids, in which a differentially protected azodicarboxylate is used together with pyrrolidinyl tetrazole as the catalyst. The central biaryl bond is being formed by Stille coupling of two sterically demanding ortho-chloropyrroloindole fragments. The inherent flexibility of the synthetic strategy proved beneficial as the route could be adjusted smoothly during the progression of the synthesis programme. Copyright

Gold-catalyzed transformation of 2-alkynyl arylazides: Efficient access to the valuable pseudoindoxyl and indolyl frameworks

An element of surprise: A series of functionalized 2-alkynyl arylazides has beed converted into 3-substituted indoles or 2,2-disubstituted indolin-3-ones in the presence of a gold(I) complex. Various oxygen or aryl nucleophiles can be used in this process to trap the intermediate α-imino gold carbene. The structural motifs of the products are found in a large variety of biologically active compounds and natural products. Copyright

N-(indazolyl)benzamido derivatives as CDK1 inhibitors: Design, synthesis, biological activity, and molecular docking studies

A series of N-1H-indazole-1-carboxamides has been synthesized and their effects on both CDK1 / cyclin B and the K-562 (human chronic myelogenus leukemia) cell line were evaluated. Using a computational model, we have observed that all the most active compounds 9e, f, i-n exhibited the same binding mode of purvanalol A in the ATP-binding cleft. Although they were able to moderately inhibit the leukemic cell line K-562 and to show inhibitory activity against the Cdc2-Cyclin B kinase in the low micromolar range, they turned out to be non-cytotoxic against HuDe (IZSL) primary cell cultures from human derm. These preliminary results are quite encouraging in view of the low toxicity demonstrated by the above-mentioned compounds.

Convenient and efficient method for the iodination of aromatic amines by pyridinium iodochloride

A simple and efficient method for the iodination of aromatic amines using pyridinium iodochloride (PyICl) in methanol as solvent is reported. Mild reaction conditions, short reaction time, and good to excellent yields of the product are the noteworthy advantages of the method. Pyridinium iodochloride is an efficient solid iodinating reagent and can be handled safely. Copyright Taylor & Francis Group, LLC.

Discovery of a novel indole series of EP1 receptor antagonists by scaffold hopping

We describe the medicinal chemistry approach that generated a novel indole series of EP1 receptor antagonists. The SAR of this new template was evaluated and culminated in the identification of compound 12g which demonstrated in vivo efficacy i

A TETRAHYDROQUINOLINE DERIVATIVE FOR TREATING NICOTINE CRAVING

The present invention relates to a new medical use for a compound of formula (I), pharmaceutically acceptable salts and solvates thereof and pharmaceutical compositions containing it, in the treatment of nicotine craving.

Bioisosteric modifications of 2-arylureidobenzoic acids: Selective noncompetitive antagonists for the homomeric kainate receptor subtype GluR5

2-Arylureidobenzoic acids (AUBAs) have recently been presented as the first series of selective noncompetitive GluR5 antagonists. In this paper we have modified the acidic moiety of the AUBAs by introducing different acidic and neutral groups, and similarly, we have replaced the urea linker of the AUBAs with other structurally related linkers. Replacing the acid with neutral substituents led to inactive compounds in all instances, showing that an acidic moiety is necessary for activity. Replacing the carboxylic moiety in 2a with a sulfonic acid (5c) or a tetrazole ring (5d) improved the potency at GluR5 receptors (compounds 5c and 5d showed IC50 values of 1.5 and 2.0 μM, respectively, compared to compound 2a with IC50 = 4.8 μM). Compound 5c did not show improved in vivo activity in the ATPA rigidity test compared to 2a, whereas compound 5d was 4 times more potent than 2a. All compounds wherein the urea linker had been replaced showed lower or no activity. The results described extend the knowledge of structure-activity relationships for the AUBAs, and compound 5d may prove to be a good candidate for studying GluR5 receptors in vitro and in vivo.