Synthesis, spectral and biological evaluation of some new heterocyclic derivatives incorporating dihydroanthracene moiety

Jumat Salimon, Nadia Salih, Emad Yousif

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

The reaction of anthrone 1 with 4-aminoantipyrine and thiosemicarbazide afforded 4-(anthracen-9(10H)-ylideneamino)-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one 2 and anthracen-9(10H)-one thiosemicarbazone 5, respectively. Oxidation of compound 2 with potassium permanganate gave 4-(anthracen-9(10H)-ylideneamino)-1-methyl-3-oxo-2-phenyl-2,3-dihydro-1H pyrazole-5-carboxylic acid 3 which on reaction with o-phenylenediamine gave 4-(anthracen-9(10H)-ylideneamino)-5-(1H-benzimidazol-2-yl)-1-methyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one 4. Furthermore, compound 5 was condensed with different substituted phenacyl bromide to give a series of 2-(anthracen-9(10H)-ylidenehydrazono)-5-substituted-2,3-dihydro-1H-thiazole 6a-g. Compound 5 also reacted with chloroacetic acid affording 2-(anthracen-9(10H)-ylidenehydrazono)thiazolidin-4-one 7. The structures of all the products have been determined by elemental analysis and spectral studies. All compounds have been screened for their antibacterial and antifungal studies. The results are summarized in Tables 1 and 2.

Original languageEnglish
Pages (from-to)399-406
Number of pages8
JournalJournal of King Saud University - Science
Volume23
Issue number4
DOIs
Publication statusPublished - Oct 2011

Fingerprint

Ampyrone
Potassium Permanganate
Thiosemicarbazones
Antipyrine
Thiazoles
Carboxylic Acids
Derivatives
Oxidation
Chemical analysis
anthrone
pyrazole
thiosemicarbazide
phenacyl bromide
chloroacetic acid
1,2-diaminobenzene

Keywords

  • Antibacterial
  • Antifungal
  • Antipyrine
  • Benzimidazole
  • Thiazole
  • Thiazolidin-4-ones

ASJC Scopus subject areas

  • General

Cite this

Synthesis, spectral and biological evaluation of some new heterocyclic derivatives incorporating dihydroanthracene moiety. / Salimon, Jumat; Salih, Nadia; Yousif, Emad.

In: Journal of King Saud University - Science, Vol. 23, No. 4, 10.2011, p. 399-406.

Research output: Contribution to journalArticle

@article{04b90809cbb542989d94cdd277cbb96c,
title = "Synthesis, spectral and biological evaluation of some new heterocyclic derivatives incorporating dihydroanthracene moiety",
abstract = "The reaction of anthrone 1 with 4-aminoantipyrine and thiosemicarbazide afforded 4-(anthracen-9(10H)-ylideneamino)-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one 2 and anthracen-9(10H)-one thiosemicarbazone 5, respectively. Oxidation of compound 2 with potassium permanganate gave 4-(anthracen-9(10H)-ylideneamino)-1-methyl-3-oxo-2-phenyl-2,3-dihydro-1H pyrazole-5-carboxylic acid 3 which on reaction with o-phenylenediamine gave 4-(anthracen-9(10H)-ylideneamino)-5-(1H-benzimidazol-2-yl)-1-methyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one 4. Furthermore, compound 5 was condensed with different substituted phenacyl bromide to give a series of 2-(anthracen-9(10H)-ylidenehydrazono)-5-substituted-2,3-dihydro-1H-thiazole 6a-g. Compound 5 also reacted with chloroacetic acid affording 2-(anthracen-9(10H)-ylidenehydrazono)thiazolidin-4-one 7. The structures of all the products have been determined by elemental analysis and spectral studies. All compounds have been screened for their antibacterial and antifungal studies. The results are summarized in Tables 1 and 2.",
keywords = "Antibacterial, Antifungal, Antipyrine, Benzimidazole, Thiazole, Thiazolidin-4-ones",
author = "Jumat Salimon and Nadia Salih and Emad Yousif",
year = "2011",
month = "10",
doi = "10.1016/j.jksus.2010.08.009",
language = "English",
volume = "23",
pages = "399--406",
journal = "Journal of King Saud University - Science",
issn = "1018-3647",
publisher = "King Saud University",
number = "4",

}

TY - JOUR

T1 - Synthesis, spectral and biological evaluation of some new heterocyclic derivatives incorporating dihydroanthracene moiety

AU - Salimon, Jumat

AU - Salih, Nadia

AU - Yousif, Emad

PY - 2011/10

Y1 - 2011/10

N2 - The reaction of anthrone 1 with 4-aminoantipyrine and thiosemicarbazide afforded 4-(anthracen-9(10H)-ylideneamino)-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one 2 and anthracen-9(10H)-one thiosemicarbazone 5, respectively. Oxidation of compound 2 with potassium permanganate gave 4-(anthracen-9(10H)-ylideneamino)-1-methyl-3-oxo-2-phenyl-2,3-dihydro-1H pyrazole-5-carboxylic acid 3 which on reaction with o-phenylenediamine gave 4-(anthracen-9(10H)-ylideneamino)-5-(1H-benzimidazol-2-yl)-1-methyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one 4. Furthermore, compound 5 was condensed with different substituted phenacyl bromide to give a series of 2-(anthracen-9(10H)-ylidenehydrazono)-5-substituted-2,3-dihydro-1H-thiazole 6a-g. Compound 5 also reacted with chloroacetic acid affording 2-(anthracen-9(10H)-ylidenehydrazono)thiazolidin-4-one 7. The structures of all the products have been determined by elemental analysis and spectral studies. All compounds have been screened for their antibacterial and antifungal studies. The results are summarized in Tables 1 and 2.

AB - The reaction of anthrone 1 with 4-aminoantipyrine and thiosemicarbazide afforded 4-(anthracen-9(10H)-ylideneamino)-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one 2 and anthracen-9(10H)-one thiosemicarbazone 5, respectively. Oxidation of compound 2 with potassium permanganate gave 4-(anthracen-9(10H)-ylideneamino)-1-methyl-3-oxo-2-phenyl-2,3-dihydro-1H pyrazole-5-carboxylic acid 3 which on reaction with o-phenylenediamine gave 4-(anthracen-9(10H)-ylideneamino)-5-(1H-benzimidazol-2-yl)-1-methyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one 4. Furthermore, compound 5 was condensed with different substituted phenacyl bromide to give a series of 2-(anthracen-9(10H)-ylidenehydrazono)-5-substituted-2,3-dihydro-1H-thiazole 6a-g. Compound 5 also reacted with chloroacetic acid affording 2-(anthracen-9(10H)-ylidenehydrazono)thiazolidin-4-one 7. The structures of all the products have been determined by elemental analysis and spectral studies. All compounds have been screened for their antibacterial and antifungal studies. The results are summarized in Tables 1 and 2.

KW - Antibacterial

KW - Antifungal

KW - Antipyrine

KW - Benzimidazole

KW - Thiazole

KW - Thiazolidin-4-ones

UR - http://www.scopus.com/inward/record.url?scp=82955214030&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=82955214030&partnerID=8YFLogxK

U2 - 10.1016/j.jksus.2010.08.009

DO - 10.1016/j.jksus.2010.08.009

M3 - Article

VL - 23

SP - 399

EP - 406

JO - Journal of King Saud University - Science

JF - Journal of King Saud University - Science

SN - 1018-3647

IS - 4

ER -