Indian Journal of Chemistry

 

Sect. B: Organic Chemistry including Medicinal Chemistry

Total visitors: 2,154  since 28-10-05

VOLUME 44 B

NUMBER 10

OCTOBER 2005


CONTENT

Papers

 

 

 

2077

Thiophene-fused quinoline analogues: Facile synthesis of 3-amino-2-cyanothieno [2, 3-b] quino­lines from 2-chloro-3-cyanoquinolines

 

IPC: Int.Cl.7 C 07 D 215/00

Starting from 2-chloro-3-cyanoquinolines, a series of 3-amino-2-cyanothienoquinolines has been prepared by treatment with Na2S followed by   ClCH2CN and K2CO3 in DMF.

 

 

Ambika Srivastava, Atish Chandra & R M Singh*

 

 

 

 

 

 

 

2082

Synthesis of 5H-dibenzo(b,f)azepine-5-carboxylic acid [3-chloro-2-(substitutedphenyl)-4-oxoaze­ti­din-1-yl]amide from 5H-dibenzo(b,f) azepine-5-car­bonyl chloride

 

IPC: Int.Cl.7 C 07 D

A synthetic approach has been established for the preparation of 5H-dibenzo(b,f)azepine-5-carboxylic acid [3-chloro-2-(substitutedphenyl)-4-oxoazetidin-1-yl]amide from 5H-dibenzo(b,f)azepine-5-carbonyl chloride alongwith their characterization.

 

 

Pralav V Bhatt & Pravin M Patel*

 

 

 

 

 

 

 

2087

Spectral studies on some cyanomethylene derivatives of cis-2,6-diaryltetrahydrothiopyrans

 

IPC: Int.Cl.7 C 07 D 335/02

 

1H and 13C NMR spectra have been recorded for 4-dicyanomethylene-cis-2,6-diaryltetrahydrothiopyrans 7-10, 4-cyano(ethoxycarbonyl)methylene-cis-2,6-diaryl­tetra­­hydrothiopyrans 11, 12 and cis-2,6-diaryl­tetra­hydrothiopyran- 4-ones 4-6 and analysed.

 

 

A  Manimekalai*  &  J  Anusuya

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

2093

Rapid and efficient synthesis of some biological active 2-azetidinones under microwave irradiation

 

IPC: Int.Cl.7 C 07 D // A 61 P 31/04, 31/10

2-Azetidinones 4a-j have been prepared by the reaction of Schiff bases 3a-j with chloroacetyl chloride and triethylamine. The reaction is carried out by conventional and microwave method.

 

 

 

 

 

 

 

 

 

K G Desai* & K R Desai

 

 

 

 

 

 

 

2097

Synthesis of some novel pharmacologically active Schiff bases using microwave method and their derivatives formazans by conventional method

 

IPC: Int.Cl.7 C 07 D // A 61 P 31/10

Schiff bases 3a-j have been prepared by the condensation reaction of p-nitrobenzoylhydrazide 1 and substituted aromatic aldehydes 2. Schiff bases
3a-j on condensation with diazonium salt of 6-methoxy-2-aminobenzothiazole yield formazans 4a-j.

 

 

 

 

 

 

 

 

Krunal G Desai* & K R Desai

 

 

 

 

 

 

 

 

 

 

 

 

 

2102

Facile synthesis and fungicidal activity of novel 4,4'-bis[2''-(5'''-substituted rhodanin-3'''-yl)thia­zol-4"-yl]bibenzyls

 

IPC: Int.Cl.7 C 07 D // A 61 P 31/10

Synthesis of 4,4'-bis[2''-(5'''-substituted rhodanin-3'''-yl)thiazol-4"-yl]bibenzyls 5a-p by conventional method as well as under microwave irradiation with excellent yield has been reported. The rate of the reaction is enhanced 230 times with MWI in comparison with conventional method. Antifungal screening results on Fusarium oxysporum and Penicillium citrinum show that most of the synthesized compounds display promising antifungal activity.

 

 

I R Siddiqui*, Pravin K Singh, Jaya Singh &

Jagdamba Singh

 

 

 

 

 

 

 

2107

Synthesis of some 3,5-diphenyl-4H-1,2,4-triazole derivatives as antitumor agents

 

IPC: Int.Cl.7 C 07 D 249/04 // A 61 P 35/00

A series of 4-arylidenamino-4H-1,2,4-triazoles 2-14 and 4-(1-aryl)ethylidenamino-4H-1,2,4-triazoles 28-30 have been synthesized by the treatment of 4-amino-4H-1,2,4-triazole 1 with certain aldehydes and ketones. Compounds 2-14 and 28-30 have been reduced with NaBH4 to afford the corresponding 4-arylmethylamino-4H-1,2,4-triazoles 15-27 and 4-(1-aryl) ethylamino-4H-1,2,4-triazoles 31-33. The compounds 2-33 have been characterized by 1H NMR, 13C NMR, IR, mass and UV spectral data. Compounds 12, 17, 18, 19, 20, 21, 22, 24, 29 and 32 have been tested for anticancer activities by the National Cancer Institute (NIH), USA. The tumor growth inhibitory potentials of the compounds are found to be low.

 

 

Olcay Bekircan* & Nurhan Gümrükçüoğlu

 

 

 

 

 

 

 

 

 

 

 

 

 

2114

Synthesis, characterization and antibacterial activity studies on some fluorine containing quinoline-4-carboxylic acids and their derivatives

 

IPC: Int.Cl.7 C 07 D 215/00 // A 61 P 31/04

Synthesis and antibacterial activity studies on some quinoline carboxylic acids and their heterocyclic derivatives have been reported. Preliminary results indicate the promising activity for some of the compounds.

 

 

 

 

 

 

B Shivarama Holla*, K Narayana Poojary,

Boja Poojary, K Subrahmanya Bhat &

N Suchetha Kumari

 

 

 

 

 

 

 

2120

Synthesis and biological activity of some 3-imidazo[1,2-a]pyridin-2-yl-chromen-2-one and 3-indolizin-2-yl-chromen-2-one

 

IPC: Int.Cl.7 C 07 D 209/04 // A 61 P 31/06, 31/12, 35/00

 

2-aminopyridines 2 in the solid state under solvent-free conditions yield 3-imidazo[1,2-a]pyridin-2-yl-chromen-2-ones 3. Condensation of 3-(2-bromo­acetyl)­coumarin 1 with 2-methylpyridines in dry benzene affords N-alkyl pyridinium salts 5. These undergo cyclization reaction when heated with sodium bicarbonate to give indolizins 6. The structures of newly prepared compounds have been confirmed from analytical and spectral data. Some of the compounds exhibit antitubercular, antiviral and anticancer activities.

 

 

 

 

 

 

P Vijaya Kumar & V Rajeswar Rao*

 

 

 

 

 

 

 

 

 

 

 

 

 

2126

Synthesis and antineoplastic activity of some
16-benzylidene substituted steroidal oximes

 

IPC: Int.Cl.7 C 07 J // A 61 P

Steroidal oximes 20-35 have been synthesized using androstene as the starting material and tested in vitro using Hollow Fiber anticancer assay at NCI, Bethesda USA. The compounds 24-28 and 30-33 have been found to be active.

 

 

 

 

Sonal Dubey, Dharam Paul Jindal &

Poonam Piplani*

 

 

 

 

 

 

 

2138

Transition states for hydride and methyl 1,2-migrations in carbene rearrangements to alkenes: An AM1 SCF-MO study

 

IPC: Int.Cl.7 C 07 C

 

 

 

 

 

Peter G S Dkhar & R H Duncan Lyngdoh*

 

 

 

 

 

Notes

 

 

 

2149

Synthesis of novel spiro-2-isoxazolines derived from parthenin

 

IPC: Int.Cl.7 C 07 D

 

 

 

 

 

Biswanath Das*, C Ramesh, N Ravindranath,

G Mahender & Harish Holla

 

 

 

 

 

 

 

 

 

 

 

 

 

2152

Microwave induced solvent-free synthesis of substituted 1,5-benzodiazepine derivatives

 

IPC: Int.Cl.7 C 07 D

An efficient synthesis of 1,5-benzodiazepines in an  eco-friendly environment of microwave irradiation  using MCM-41 zeolite as catalyst is described

 

 

 

 

 

 

 

K Sucheta & B Vittal Rao*

 

 

 

 

 

 

 

2155

Microwave assisted one pot synthesis of 8-methyl-3,6,9-triphenyl-5,6-dihydro-9H-pyrazolo[3,4-e]­[1,2,4]triazolo[3,4-b][1,3,4]thiadiazepine

 

IPC: Int.Cl.7 C 07 D

A convenient simple one step synthesis of 8-methyl-3,6,9-triphenyl5,6-dihydro-9H-pyrazolo [3,4-e]­[1,2,4]­triazolo[3,4-b][1, 3, 4]thiadiazepin es 3a-l from (4E)-4-benzylidene-5-methyl-2-phenyl-3, 4-dihydro­pyrazol-3, (2H)-ones 1a-f and 4-amino-5-phenyl-4H-1,2,4-tri­azole-3-thiols 2a-b have been reported.

 

 

 

 

 

 

B P Nandeshwarappa, D B Aruna Kumar, H S Bhojya Naik,V P Vaidya & K M Mahadevan*

 

 

 

 

 

 

 

 

 

 

 

 

 

2158

Clean and efficient microwave solvent-free synthesis of some antimicrobial compounds from 2-aminothiadiazine

 

IPC: Int.Cl.7 C 07 D // A 61 P 31/04

A series of 1-[5΄-(2,4-dichloro-5-fluorophenyl)-6΄H-1΄,3΄,4΄-thiadiazin-2΄-yl]-4-(substituted phenyl)-3-chloro-2-oxo-azetidines 3 and 3-[5΄-(2,4-dichloro-5-fluorophenyl)-6΄H-1΄,3΄,4΄-thiadiazin-2΄-yl]-2-(substi­tuted­phenyl)-1, 3-thiazolidin-4-one 4 have been synthesized using environmentally benign procedure and evaluated for their antimicrobial activity. Neat reactants are subjected to microwave irradiation under solvent-free condition.

 

 

V M Patel & K R Desai*

 

 

 

 

2163

Synthesis and antimicrobial screening of 2'-hydroxy-5'-(phenylazo)-N-(1",3"-diketophenyl­amine)-3-chloroazetidin-2-ones

 

IPC: Int.Cl.7 C 07 D // A 61 P 31/04

A series of 2˘-hydroxy-5˘-(phenylazo)-N-(1˘˘,3˘˘-dike­to­phenylamine)-3-chloro azetidin-2-ones 2 have been synthesized and evaluated for their antimicrobial activity.

 

 

 

Anand K Halve*, Poonam Gour, Rakesh Dubey, Deepti Bhadauria & Bhuwan Bhaskar

 

 

 

 

 

 

 

 

 

 

 

 

 

2166

Synthesis and antibacterial evaluation of some theophylline derivatives

 

IPC: Int.Cl.7 C 07 D // A 61 P 31/04

Theophylline N-alkoxy aryl biguanides 8a-d have been prepared by condensing corresponding N-alkoxyamine salt 6a-c with substituted aryl-dicyandiamide. In an another attempt N-allyl theophylline 9 is brominated and condensed with double mole ratio of N-hydroxyphthalimide to obtain 2,3-bis-oxyphthalimido-1-theophylline propane 11.

 

 

 

 

Kavita Rathore, Ritu Vyas & G L Talesara*

 

 

 

 

 

 

 

2171

Synthesis and bioactivity of some new 2-substi­tuted-3,4-dihydro-3-(3˘-chloro-4˘-fluoro­phenyl)-2H-[1,3,2]benzoxaza­phosphorin 2-oxides

 

IPC: Int.Cl.7 C 07 D // A 61 P 31/04, 31/10

 

 

 

 

 

Y B Kiran, M Kasthuraiah, C Nagaraju, D Gunasekar, S V S Madhu Babu&

C Devendranath Reddy*

 

 

 

 

 

 

 

 

 

 

 

 

2178

Novel clay-catalysed expeditious cyclization to
bis-benzothiazepine

 

IPC: Int.Cl.7 C 07 D // A 61 P 31/10

 

Synthesis of 4,4˘-bis(2"-aryl-2",3"-dihydro-1",5"-ben­zo­thiazepine-4"-yl)bibenzyls 3a-j under microwave irradiation with excellent yield has been reported. Antifungal screening results of 3a-j on Fusarium oxysporum and Penicillium citrinum show that most of the synthesized compounds display promising antifungal activity.

 

 

 

 

 

 

 

 

 

 

 

Pravin K Singh*, Vishal Srivastava, J Singh & I R Siddiqui

 

 

 

 

 

 

 

2183

A practical and efficient method for the prepara­tion of aromatic sulfones by the reaction of aryl sulfonyl chlorides with arenes catalysed by Fe(OH)3

 

IPC: Int.Cl.7 C 07 C

Fe(OH)3 catalyses Friedel-Crafts sulfonylation of arenes with arylsulfonyl chlorides to obtain the corresponding diaryl sulfones in good yields.

 

 

 

 

 

 

 

 

 

 

Tongshou Jin*, Ying Zhao, Yanran Ma & Tongshuang Li

 

 

 

 

 

 

 

 

 

 

 

 

 

2186

Bioactive compounds from the Indian ocean gorgonian Subergorgia suberosa (Pallas)

 

IPC: Int.Cl.7 A 61 K 35/00

From the gorgonian S. suberosa Pallas collected from the Mandapam coast, Tamil Nadu, a monohydroxy sterol mixture, subergorgic acid 1, batyl alcohol 2, two pregnane derivative mixtures, thymine 3, and a new ceramide mixture in which N-hexadecanoyl-2-amino-1,3-dihydroxyoctadec-4-ene 6 is the major isomer, have been isolated. Compounds 1, 3, 6 and one of the pregnane mixtures exhibit antibacterial and antifungal activities.

 

 

C Subrahmanyam*, S Ratna Kumar &

G Damodar Reddy

 

 

 

 

Authors for correspondence are indicated by (*)

IPC: International Patent Classification

Int. Cl7.: International Classification, 7th Edition, 1999