A Practical Iodination of Aromatic Compounds by Using Iodine and Iodic Acid

Shinde, Avinash; Zangade, Sainath; Chavan, Shivaji B.; Vibhute, Archana Y.; Nalwar, Yogesh S.; Vibhute, Yeshwant B.

doi:10.1080/00397910903457332

Cited by 24 publications

(15 citation statements)

References 15 publications

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“…In continuation of earlier research work [16][17][18][19], we report here in a simple, rapid, efficient and environmentally benign solvent-free iodination of 2-acetyl-1-naphthol using iodine and iodic acid in combination with grinding at room temperature. The iodination occur selectively at electron rich centre i.e.…”

Section: Resultsmentioning

confidence: 94%

Selective iodination of 2-acetyl-1-naphthol using iodine and iodic acid under solvent-free grinding technique

Zangade¹,

Mokle

Shinde

et al. 2012

Eur. J. Chem.

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Section: Resultsmentioning

confidence: 94%

Selective iodination of 2-acetyl-1-naphthol using iodine and iodic acid under solvent-free grinding technique

Zangade¹,

Mokle

Shinde

et al. 2012

Eur. J. Chem.

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“…Biaryl bromide 36 was obtained from the SuzukieMiyaura cross coupling [54] between pinacolboronic ester 35 [57] and 1,3-dibromobenzene and converted to azide 17 using the Liang's protocol. (Scheme 5) Preparation of azide 19 started with ortho-iodination [58] of pnitroaniline 37, followed by protection of amino group of the resulting iodide 38 as acetamide 39 [59] and subsequent SuzukieMiyaura coupling with 1-naphtylboronic acid [60] to deliver biarylic compound 40 in 82% yield over three steps. The transformation of nitro derivative 40 to the corresponding azide 42 was performed in 2 steps via aniline 41 [61,62].…”

Section: Preparation Of Azides 15e21mentioning

confidence: 99%

Ynamide Click chemistry in development of triazole VEGFR2 TK modulators

Vojtíčková

Dobiáš

Hanquet

et al. 2015

European Journal of Medicinal Chemistry

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Keywords:Oxazole/1,2,3-triazole isosteric replacement Ynamide CuACC Click chemistry VEGFR2 tyrosine kinase inhibition Cytotoxic activity in Huh-7 and Mahlavu hepatocellular carcinoma cell lines PI3K/Akt pathway a b s t r a c t Structure novelty, chemical stability and synthetic feasibility attracted us to design 1,2,3-triazole compounds as potential inhibitors of VEGFR2 tyrosine kinase. Novel triazoles T1eT7 were proposed by oxazole (AAZ from PDB: 1Y6A)/1,2,3-triazole isosteric replacement, molecular modelling and docking. In order to enable synthesis of T1eT7 we developed a methodology for preparation of ynamide 22. Compound 22 was used for all Click chemistry reactions leading to triazoles T1eT3 and T6eT7. Among the obtained products, T1, T3 and T7 specifically bind VEGFR2 TK and modulate its activity by concentration dependent manner. Moreover predicted binding poses of T1eT7 in VEGFR2 TK were similar to the one known for the oxazole inhibitor AAZ (PDB: 1Y6A). Unfortunately the VEGFR2 inhibition by triazoles e.g. T3 and T7 is lower than that determined for their oxazole bioisosters T3-ox and AAZ, resp. Different electronic properties of 1,2,3-triazole/oxazole heterocyclic rings were proposed to be the main reason for the diminished affinity of T1eT3, T6 and T7 to an oxazole AAZ inhibitor binding site in VEGFR2 TK (PDB: 1Y6A or 1Y6B). Moreover T1eT3 and T6 were screened on cytotoxic activity against two human hepatocellular carcinoma cell lines. Selective cytotoxic activity of T2 against aggressive Mahlavu cells has been discovered indicating possible affinity of T2 to Mahlavu constitutionally active PI3K/Akt pathway.

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“…The starting iodoanilines required for the preparation of imines were prepared by iodination of substituted anilines using molecular iodine and iodic acid by refluxing technique [28]. Bromination of 3,4-dimethoxybenzaldehyde was carried out using Br2/acetic acid as brominating agent to yield 3-bromo-4,5-dimethoxybenzaldehyde.…”

Section: Synthesismentioning

confidence: 99%

Synthesis and antimicrobial activity of some novel 2-azetidinones and 4-thiazolidinones derivatives

et al. 2013

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KEYWORDSSeveral 2-azetidinones 2a-e and 4-thiazolidinones 3a-e have been synthesized from halosubstituted Schiff bases using conventional as well as microwave technique. The newly synthesized compounds were established on the basis of spectroscopic technique. Further, all compounds screened for antimicrobial activity against Bacillus subtilis, Escherichia coli, Aspergillus niger and Aspergillus flavus. Most of the titled compounds show potent activity.

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A Practical Iodination of Aromatic Compounds by Using Iodine and Iodic Acid

Cited by 24 publications

References 15 publications

Selective iodination of 2-acetyl-1-naphthol using iodine and iodic acid under solvent-free grinding technique

Selective iodination of 2-acetyl-1-naphthol using iodine and iodic acid under solvent-free grinding technique

Ynamide Click chemistry in development of triazole VEGFR2 TK modulators

Synthesis and antimicrobial activity of some novel 2-azetidinones and 4-thiazolidinones derivatives

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