Azoles and bis-Azoles: Synthesis and Biological Evaluation as Antimicrobial and
Anti-cancer Agents
Kheder, NA [ 1,2 ]; Riyadh, SM [ 1,3 ]; Asiry, AM [ 3 ]
CHEMICAL & PHARMACEUTICAL BULLETIN
Volume: 61, Issue: 5, Pages: 504-510, Published: MAY 2013
Publisher PHARMACEUTICAL SOC JAPAN, 2-12-15 SHIBUYA, SHIBUYA-KU, TOKYO,
150-0002, JAPAN
ISSN: 0009-2363
Abstract
Novel hydrazonoyl halides 3, 5 and bis-hydrazonoyl halides 7, 9 were synthesized. The
synthetic utility of bis-hydrazonoyl halide 7 was explored to prepare novel bis-azole 13
with antipyrine moiety. On the other hand, [1,3,4]thiadiazol-2(3H)-ylidene 17 and
thiazol-2(3H)-ylidene 21 derivatives, with antipyrine moiety, were prepared from the
reaction of 3-mercapto-3-(phenylamino)acrylamide derivative 10 with N-phenyl
benzenecarbohydrazonoyl chloride (14) and 3-(2-bromoacetyl)-2H-chromen-2-one (18),
respectively. The structures of the isolated products were confirmed by spectral data (IR,
H-1-NMR, C-13-NMR, MS) and elemental analyses. The anti-cancer activitiy of the
synthesized products against the colon carcinoma (HCT) cell line was determined and
the results revealed promising activity of compound 3. In addition, the antimicrobial
activity of some selected products was evaluated. The results proclaimed that
compounds 9, 17, and 21 have high antibacterial activity against Gram-positive bacteria
(SA, BS) and Gram-negative bacteria (PA, EC).
Keywords
Author Keywords:anti-cancer activity; antimicrobial activity; antipyrine; azole; bis-azole
KeyWords Plus:INCORPORATING ANTIPYRINE MOIETY; REGIOSELECTIVE
SYNTHESIS; CONVENIENT SYNTHESIS; ANTIVIRAL ACTIVITY;
ANTITUMOR-ACTIVITY; DERIVATIVES; ANTIBACTERIAL; HETEROCYCLES;
THIOPHENE; FACILE
Author Information
Reprint Address: Riyadh, SM E-mail Addresses:riyadh1993@hotmail.com
Cairo Univ, Fac Sci, Dept Chem, Giza 12613, Egypt.
Organization-Enhanced Name(s)
Cairo University
Addresses:
[ 1 ] Cairo Univ, Fac Sci, Dept Chem, Giza 12613, Egypt
Organization-Enhanced Name(s)
Cairo University
[ 2 ] King Khalid Univ, Fac Pharm, Dept Pharmaceut Chem, Abha 9004, Ksa, Saudi
Arabia
Organization-Enhanced Name(s)
King Khalid University
[ 3 ] King Khalid Univ, Fac Sci, Dept Chem, Abha 9004, Ksa, Saudi Arabia
Organization-Enhanced Name(s)
King Khalid University