Indian Journal of Chemistry

Sect. B: Organic Chemistry including Medicinal Chemistry

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VOL. 49B

NUMBER 8

August 2010

CONTENTS

Papers

 

 

 

1071

General approach to 2,4-dialkyl-3-carboxy­buty­rolactones: An efficient synthesis of (±)-striatis­porolide A and (±)-lichesterinic acid

Starting from 2-alkylidene-3-methylsuccinimides, simple and efficient synthesis of the natural products striatisporolide A, lichesterinic acid and lichesterylic acid have been demonstrated via an acid catalyzed hydrolysis, esterification, OsO4-dihydroxylation and dehydrative cyclization pathway.

 

 

 

 

Ramesh M Patel & Narshinha P Argade*

 

Division of Organic Chemistry, National Chemical Laboratory, Pune 411 008, India

 

 

 

 

 

 

1076

Synthesis and anti-inflammatory activity evalua­tion of some sulfonamide and amidine derivatives of 4-aryl-3-(2 or 4-picolyl)-2-imino-4- thiazolines

Several sulfonamide and amidine derivatives of 4-aryl-3(2 or 4-picolyl)-2-imino-4-thiazolines have been synthesized and screened for anti-inflammatory activity. Compound 6a exhibits anti-inflammatory activity comparable to standard drug ibuprofen.

 

 

 

6a

 

 

Sham M Sondhi*, Amrender Dhar Dwivedi,
Jaiveer Singh & P P Gupta

 

Department of Chemistry, Veer Narmad South Gujarat University, Surat 395 007, Gujarat, India

 

 

 

 

 

 

 

 

 

 

 

 

1083

Synthesis and biological activity of 6-alkyl/chloro-3-(4-(6-alkyl/chloro-2H-benzo-[e][1,3]oxazin-3(4H)-yl)phenyl)-3,4-dihydro-2H- benzo[e][1,3]oxazines

The efficient synthesis of symmetrical bis-benzoxazines using microwave irradiation is described and the possibility of a multicomponernt approach to the target molecule has also been explored. The antimicrobial studies on the synthesized benzoxazines have been investigated.

 

 

 

 

 

 

 

 

 

 

 

Ramayan Manikannan & Shanmugam Muthusubramanian*

 

Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, India

 

 

 

 

 

 

1088

Synthesis and biological activity of novel 2,5-disubstituted-1,3,4-oxadiazoles

1,3,4-Oxadiazoles incorporating halo pyridines have been synthesized starting from substituted pyridinyloxy benzalde­hydes, by converting them in to corresponding arylidene hydrazides followed by chloramine-T oxidation to the title compounds. The 2,5-disubstituted 1,3,4-oxadiazole derivatives showed promising antibacterial activity.

 

 

 

 

 

 

 

 

 

 

M Shailaja, M Anitha, A Manjula & B Vittal Rao*

Organic Division II, Indian Institute of Chemical Technology, Hyderabad 500 007, India

 

 

 

 

 

 

 

 

 

 

 

 

1098

1,3-Di-peptido-conjugates of calix[4]arene and its di-OCH3 derivatives: Synthesis, characterization and phosphate recognition

Novel double-armed peptido-conjugates of calix[4]arene have been developed on the lower rim of the macrocycle. The functional group pendants exhibit conformational bend through the involvement of 11-atom N-H…O hydrogen bond inscribed in a 14-atom O-H…O interaction. As a result, only the terminal -COOR and -COOH groups are exposed to the environment, but not the amide moiety. Conformational mobility induced by the replacement of lower rim phenolic–OH by –OCH3 has been demonstrated by variable temperature NMR studies in the corresponding –OCH3 derivatives. Differential receptor binding characteristics of these conjugates towards phosphate are demonstrated using absorption spectroscopy. The negatively charged phosphate group is received preferentially by the carboxylic terminal over the ester terminal conjugate.

 

 

 

 

Mishtu Dey, Amjad Ali, Amitabha Acharya & Chebrolu P Rao*

 

Bioinorganic Laboratory, Department of Chemistry, Indian Institute of Technology Bombay,
Powai, Mumbai 400 076, India

 

 

 

 

 

 

1109

Synthesis of a new series of quinolinyl chalcones as anticancer and anti-inflammatory agents

 

A new series of quinolinyl chalcones SGCH 1-20 are synthesized from the combination of different quinolines and substituted aromatic aldehydes which exhibited potent anticancer and anti-inflammatory activity.

 

 

 

 

Vijay Kotra, S Ganapaty* & Srinivas R Adapa

 

College of Pharmaceutical Sciences, Andhra University, Visakhapatnam 530 003, India.

 

 

 

 

 

 

 

 

 

 

1117

Synthesis and anti-microbial activity of (Z)-4-(4-substituted-thiazol-2-yl)-1-(2-oxoindolin-3-ylide­ne) semicarbazide and its derivatives

 

The compounds 6-8a,b, and 9a-f have been prepared by (Z)-4-(4-substitutedthiazol-2-yl)-1-(2-oxoindoline-3-ylidene)semi­car­­ba­­­­zides 5a,b and screened for their antimicrobial activities.

 

 

 

 

 

 

 

5a,b

 

 

 

 

 

 

 

S M Basavarajaiah & B H M Mruthyunjayaswamy*

 

Department of Studies and Research in Chemistry, Gulbarga University, Gulbarga 585 106, India

 

 

 

Notes

 

 

 

1127

An efficient and solvent-free one-pot synthesis of nitriles from aldehydes

 

Aldehydes are converted into corresponding nitriles in high yields by a one-pot solvent-free reaction with hydroxylamine hydrochloride in the presence of catalytic amount of pyridine under microwave irradiation. The reactions go to completion within one minute. The process is green, efficient and inexpensive.

 

 

 

 

 

 

 

 

 

 

 

M A Pasha* & Aatika Nizam

 

Department of Studies in Chemistry, Central College Campus,

Bangalore University, Bangalore 560 001, India

 

 

 

 

 

 

 

 

 

 

 

 

1130

Microwave assisted synthesis of 1,3,4-oxadiazoles carrying benzimidazole moiety and their anti­microbial properties

 

Microwave assisted synthesis, biological activity of a series of 1-{[5-(4-substituted aryl)-1,3,4-oxadiazol-2-yl]methyl}-2-pro­pyl-1H-benzimidazoles and 2-benzyl-1-{[5-(4-substituted aryl)-1,3,4-oxadiazol-2-yl]methyl}-1H-benzimidazoles are described.

 

 

 

 

 

Janardhana Gowda, A M A Khadar*, Balakrishna Kalluraya &

Nalilu Suchetha Kumari

 

Department of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India

 

 

 

 

 

 

 

1135

Facile chemoselective synthesis of novel 6-aryl-12H-indolo[2,3-e][1,4]benzodiazocine derivatives by the reaction of 3-aroylmethylene-2H-indol-2-ones with o-phenylene-diamine

 

Novel syntheses of 6-aryl-12H-indolo[2,3-e][1,4]­benzo­dia­zocine derivatives have been achieved for the first time by the reaction of 3-aroylmethylene-2H-indol-2-ones with o-phenyl­ene­diamine. While the analogous reaction with ethylene diamine resulted in exclusive formation of Schiff base deri­vatives viz. 1,3-dihydro-3-[2-(2-aminoethyl-imino)-2-aryl-ethylidene]indol-2-ones.

 

 

 

 

 

Pahup Singh*, Anshu Dandia & Poonam Khandelwal

 

Centre of Advanced Studies, Department of Chemistry, University of Rajasthan, Jaipur, India.

 

 

 

 

 

 

 

 

 

 

 

 

 

1140

Mixed ligand cobalt(II) complex as an efficient catalyst for oxidative deoximation using hydrogen peroxide

 

Mixed ligand Cobalt(II) complexes are reported to decompose hydrogen peroxide. This property is utilized for a simple method for deoximation of oximes. Yields are high and overoxidation is not observed. The Co(II) catalyst could be recycled.

 

 

 

 

 

 

 

 

 

 

 

 

 

Pranab J  Das*, Amal Das & Akashi Baruah

 

Department of Chemistry, Gauhati University, Guwahati 781 014, India

 

 

 

 

 

 

 

1144

Synthesis of isoxazolyl quinoline-3-carboxamides and 1,4-benzothiazine-2-carboxamides as poten­tial bioactive compounds

 

 

Synthesis of isoxazolyl quinoline-3-carboxamides 3 and isoxazolyl-1,4-benzothiazine-2-carboxamides 4 have been accomplished by cyclocondensation of isoxazolyl-3-oxo-butanamides 2 with o-amino benzaldehyde or o-amino thiophenol involving Friedelander’s condensation and oxidative cyclization respectively.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

E Rajanarendar*, K Rama Murthy, M Nagi Reddy & S Raju

 

Department of Chemistry, Kakatiya University, Warangal 506 009, India

 

 

 

 

 

 

 

 

 

 

 

 

 

1151

Synthesis and biological evaluation of some inno­vative coumarin derivatives containing thia­zoli­din-4-one ring

 

The reaction of ethyl 2-oxo-2H-chromene-3-carboxylate 3 with hydrazine and condensation of the resulting hydrazone with different aromatic aldehydes give the corresponding Schiff bases 5a-e. Reaction of these Schiff bases with mercaptoacetic acid furnishes the target thiazolidinone molecules 6a-e that have been screened for their antibacterial and analgesic activities.

 

 

 

 

 

 

 

RamaGanesh C K, Yadav D Bodke* & Venkatesh K B

 

Department of Studies and Research in Industrial Chemistry, Jnana Sahyadri,

Kuvempu University, Shankaraghatta 577 451, Karnataka, India

 

 

 

 

 

 

 

1155

A green approach in aqueous phase synthesis of isoxazolidine derivatives from N-phenyl-α-amino nitrone and their antibacterial activities

 

Environmentally benign 1,3 dipolar cycloaddition reaction of N-phenyl-α-amino nitrone with different dipolarophiles have been studied in water for the synthesis of novel isoxazolidines. Significant change in rate acceleration and high yield of these reactions are observed in water compared with organic solvents. All the synthesized compounds were screened for their antibacterial activity and have been found to exihibit significant activity.

 

 

 

 

 

Bhaskar Chakraborty*, Manjit Singh Chhetri & Amalesh Samanta

 

Organic Chemistry Laboratory, Sikkim Govt. College, Gangtok, Sikkim 737102, India

 

 

 

 

 

 

Authors for correspondence are indicated by (*)