Indian Journal of Chemistry

Sect. B: Organic Chemistry including Medicinal Chemistry

VOL. 49B

NUMBER 2

February 2010

CONTENTS

Papers

 

 

 

199

Enantioselective synthesis of diarylmethanols using microbial transformation

 

Diaryl ketones are reduced enantioselectively to the (S)-diarylmethanols using fungus Rhizopus arrhizus. The physicochemical parameters like microbe selection, reaction time, temperature, etc. for the bioreduction reactions are optimized by taking p-chloro benzophenone as a model substrate.

 

 

 

 

 

 

 

 

P R Salokhe, G S Rashinkar & R S Salunkhe*

 

Department of Chemistry, Shivaji University, Kolhapur 416 004, India

 

 

 

 

 

 

 

203

Modern Friedel-Crafts Chemistry. Part 30­1. Facile synthesis of isomeric tri- and tetramethyl­tetra­hydrophenanthrenes via rearranged cycli­alkyla­tion of suitably methylated 1-(1- and 2-naphthyl)-3-pentanols

 

Simplified Friedel-Crafts cyclialkylation approaches towards the syntheses of isomeric 1,1,2- and 3,4,4-trimethyl-1,2,3,4-tetrahydrophenanthrenes and isomeric 1,1,2,2- and 3,3,4,4-tetramethyl-1,2,3,4-tetrahydrophenanthrenes are reported.

 

 

α - or β-Naphthyl (R=H, CH3)               from α-isomer         fromβ-isomer

 

 

 

Ali Ali Khalaf *, Hassan A Albar & Khalid O El-Fouty

 

Department of Chemistry, Faculty of Science, Assiut University, Assiut, Egypt

 

 

 

 

 

 

 

 

 

 

 

 

 

209

Synthesis and antibacterial activities of some novel isoxazolidine derivatives derived from
N-phenyl-α-chloro nitrone in water

1,3 dipolar cycloaddition reaction of N-phenyl-α-chloro nitrone with different dipolarophiles have been studied in water for the synthesis of novel isoxazolidines. Significant rate acceleration and high yield of these reactions are observed in water with remarkable changes in stereo and regioselectivity compared to organic solvents. The structures of all compounds have been established on the basis of spectral and analytical data. All compounds have been screened for their antibacterial activity and found to be active.

 

 

 

Bhaskar Chakraborty*, Manjit Singh Chhetri, Saurav Kafley & Amalesh Samanta

 

Organic Chemistry Laboratory, Sikkim Govt. College, Gangtok 737 102, India

 

 

 

 

 

 

 

216

Synthesis and photochemical H-abstractions of some 2-thienyl/furyl-3-allyloxybischromones

 

Synthesis and photolysis of some bischromones built around trans-2-butene and 2-butyne have been described.

 

 

 

 

Rupesh Kumar & Mohamad Yusuf*

 

Department of Chemistry, Punjabi University, Patiala 147 002, India

 

 

 

 

 

 

224

Structural optimization of new class of selective carbonic anhydrase inhibitors: QSAR approach

 

QSAR studies on a new class of sulfonamide derivatives with selective carbonic anhydrase inhibitory activity have been performed using a combination of various physicochemical descriptors. The best equation selected emphasized on high hydrophobic groups, presence of electron donating groups, size and shape of molecule might be influencing the selective carbonic anhydrase inhibitory activity.

 

Parent Nucleus

 

Blessy Pothen, Vineet Singh, Surendra Kumar & Meena Tiwari*

 

Computer Aided Drug Design Lab, Department of Pharmacy, Shri Govindram Seksaria Institute of Technology and Science, 23, Park Road, Indore 452 003, India.

 

 

 

 

 

 

 

 

 

 

 

 

234

Facile ketone sensitized photochemical ring opening of isoxazolidines to β-enaminocarbonyl compounds

A methodology for the inter- and intramolecular ketone sensitized photochemical cleavage of ixoxazolidine moiety to furnish b-enaminocarbonyl compounds is reported. A series of experiments on isoxazolidines under different sets of irradiation conditions have been conducted to delineate the mechanistic details, in particular, the photosensitization by carbonyl moiety.

 

 

 

 

 

 

Rajinder Singh, Gurmit Singh & Mohan Paul S Ishar*

 

Bio-organic and Photochemistry Laboratory, Department of Pharmaceutical Sciences, Guru Nanak Dev University, Amritsar 143 005, India

 

 

 

 

 

 

 

 

Notes

 

 

 

 

 

 

241

Syntheses of aromatic aldehyde imine derivatives of 2-thiobenzyl-1, 3, 4-thiadiazole and evaluation of their anticonvulsant activity

 

Benzyl and chlorobenzyl substituted 1, 3, 4-thiadiazole imine derivatives have been prepared and found to show good anticonvulsant activity. Chlorobenzyl substituted compounds show potent activity against phenytoin as standard reference. Neurotoxicity has been screened through the Rota rod and ethanol potentiation test. The compounds did not show any neurotoxicity.

 

 

 

 

 

 

Bahar Ahmed* & Md. Yusuf

 

Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Jamia Hamdard, New Delhi 110 062, India

 

 

 

 

 

 

 

 

 

 

 

 

 

247

Chemoselective reaction of malononitrile with imine-ones and antifungal potential of products

 

 

 

 

 

 

 

Anjali Sidhu*, J R Sharma & Mangat Rai

 

Department of Chemistry, bDepartment of Plant Pathology, Punjab Agricultural University, Ludhiana 141 004, India

 

 

 

 

 

 

251

Photo-Fries rearrangement of naphthalene-1,5-diyl bis(4-chlorobutanoate): Exclusive and regioselective mono-rearrangement

 

Photo-Fries rearrangement of naphthalene-1,5-diyl bis(4-chlorobutanoate) provides only the mono-rearranged product with the other ester remaining intact.

 

 

 

 

 

 

K Balamurugan, M Bhama & V Sridar*

 

Industrial Chemistry Lab, Central Leather Research Institute, Adyar, Chennai 600 020, India

 

 

 

 

 

 

 

253

Potassium triiodide catalyzed Friedlander synthesis of 1,8-naphthyridines in aqueous media

 

Potassium triiodide catalyses the Friedlander condensation of 2-aminonicotinaldehyde 1 with carbonyl compounds contain­ing a-methylene group 2 in aqueous media to afford 1,8-naph­thy­­ri­dines 3 in high yields.

 

 

 

K Mogilaiah*, K Shiva Kumar & N Vasudeva Reddy

 

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

 

 

 

 

 

 

 

 

 

 

 

 

 

256

New constituents from Psoralea corylifolia

 

Two new metabolites, psoralester 1 and psorachromene 2 together with five known compounds have been isolated from the seeds of Psoralea corylifolia and their structures have been elucidated on the basis of their detailed NMR and mass spectral data.

 

 

                                                        1                                                          2

 

 

Amit Tewari & R S Bhakuni*

 

Central Institute of Medicinal and Aromatic Plants, P.O. CIMAP, Lucknow 226 015, India

 

 

 

 

 

 

 

260

A new route for the synthesis of (R)-glycer­aldehyde acetonide: a key chiral building block

 

A new route for the synthesis of (R)-glyceraldehyde acetonide via asymmetric dihydroxylation of allyl 4-methoxy benzoate using the (DHQ)2PHAL, K2OsO4·2H2O catalyst system is described. This route involves the asymmetric dihydroxylation of allyl 4-methoxy benzoate, acetonide protection of vicinyl dihydroxyl groups followed by cleavage of p-methoxy benzoate ester and subsequent oxidation to give the (R)-glyceraldehyde acetonide.

 

 

 

 

 

K Chandra Babu, G Ramadasu, L Gangaiah,  G Madhusudhan* & K Mukkanti

 

aInogent Laboratories Private Limited, A GVK BIO Company, 28A, IDA, Nacharam, Hyderabad 500 076, India

 

 

 

 

 

 

 

264

Synthesis of benzofuran analogs of fenamates as non steroidal antiinflammatory agents

 

Series of benzofuran analogs of fenamates are easily synthesized by conventional heating method. All the compounds were screened for antiinflammatory activity.

 

 

 

Balasaheb Y Mane*, Y S Agasimundin & B Shivakumar

 

SVPM’s College of Pharmacy, Malegaon BkII, Baramati 413 115, India

 

 

 

 

 

 

 

 

 

 

 

 

 

270

Ecofriendly synthesis of thieno[2,3-b]pyridines  derivativies

 

2-Aminothiophenes are readily transformed to thienopyridines using suitable solvent system.

 

 

M Kidwai*, Priya & R Poddar

 

Green Research Laboratory, Department of Chemistry, University of Delhi, North Campus, New Delhi 110 007, India.

 

 

 

 

 

Authors for correspondence are indicated by (*)