Indian Journal of Chemistry

Sect. B: Organic Chemistry including Medicinal Chemistry

VOL. 45B

NUMBER 11

NOVEMBER 2006

CONTENTS

Rapid Communications

2465

An efficient ring-closing metathesis reaction based
approach to 1,2,2-trimethylcyclopentane-methanol. Formal synthesis of (±)‑herbertene and (±)‑cuparenes

IPC: Int.Cl.⁸ C07C

Formal total synthesis of aromatic sesquiterpenes
hebertene and cuparene employing a Claisen rearrange-ment-RCM based strategy is reported.

A Srikrishna* & G Satyanarayana

2469

Substituent directed distal photoisomerisation of indolic dienyl  chromophores

IPC: Int.Cl.⁸ C07D

Photoisomerisation in indolic dienyls is controlled by the substituents present on the indolic nitrogen atom.

Anil K Singh* & Prasanta K Hota

Papers

2474

Asymmetric induction in copper (I)-catalyzed
intramolecular [2 + 2] photocycloaddition: Synthesis of enantiopure cyclobutane derivatives

IPC: Int.Cl.⁸ C07C

Asymmetric induction in copper (I)-catalyzed intramolecular [2+2] photocycloaddition of 1,6-dienes to produce enantiopure oxa-bicyclo[3.2.0]heptane derivatives has been achieved. A novel anion-induced cleavage of the tetrahydrofuran ring in these oxa-bicyclo[3.2.0]heptane derivatives has led to a convenient access to the synthetically useful cis-1,2-disubstituted cyclobutanes in enantiomerically pure form.

Niladri Sarkar & Subrata Ghosh*

2485

Phase-transfer catalyzed acylation of 5(3)-hydroxy-3(5)-substituted-1H-pyrazoles

IPC: Int.Cl.⁸ C07D

PTC-acylation of 5(3)-hydroxy-3(5)-substituted-1H-pyrazoles by different acyl halides reagents under PTC- conditions has been investigated. This work is aiming to study the comparative reactivity of N- versus O- versus C-acylation.

A Kh Khalil, M A Hassan*, M M Mohamed & A M El-Sayed

2491

The theoretical conformation analyses of polyoxanorbornene chain

IPC: Int.Cl.⁸ C07C

The conformational analysis of polyoxanorbornene (PONB) chain is investigated with the AM1, MM2, AMBER and OPLS methods taking into consideration the possibility of binding of oxanor- bornene monomers to each other at various positions, i.e. exo-exo, exo-endo, endo-endo.

                           exo-exo(A)(TCTC)                       exo-endo(B)(TGTG^-)                             endo-endo(C)(TCTC)

                    exoexo-endoendo(D)(TGTG^-)                                    exoexo-endoexo-endoendo-exoendo(E)(TGTG^-)₂

Sevil Savaşkan Yılmaz & Rıza Abbasoğlu*

2497

Exploring QSAR of peripheral benzodiazepine receptor binding affinity of 2-phenylpyra-zolo[1,5-a]pyrimidin-3-yl-acetamides using topological and physicochemical descriptors

IPC: Int.Cl.⁸ C07D

The present QSAR study has attempted to explore the structural and physicochemical requirements of 2-phenyl-pyrazolo[1,5-a]pyrimidin-3-yl-acetamides for binding with peripheral benzodiazepine receptor.

Manoj Kumar Dalai, J Thomas Leonard & Kunal Roy*

2506

Synthesis, antimicrobial and antiinflammatory activities of 1,3,4-oxadiazoles linked to naphtho[2,1-b]furan

IPC: Int.Cl.⁸ C07D

Condensation of naphtho[2,1-b]furan-2-carboxyhydrazide 1 with different aromatic aldehydes affords the corresponding arylidene derivatives 2a-h. These compounds undergo
cyclization with acetic anhydride and mercuric oxide to yield 3a-h and 4a-h respectively. The compound 1 on refluxing with carbon disulphide and ethanolic potassium hydroxide followed by acidification furnish 5. It is converted into
Mannich bases 6a-h by treatment with  formaldehyde and appropriate  aromatic  amines. The selected  compounds have  been screened for their antimicrobial and anti-inflammatory ativities. The compound 4f has exhibited considerable antimicrobial activity and the compound 4c showed significant anti-inflammatory activity.

K C Ravindra, H M Vagdevi*, V P Vaidya &
Basavaraj Padmashali

2512

Synthesis of chemiluminescent naphtho[1,8-de][1,2]diaze-
pine-1,4-diones

IPC: Int.Cl.⁸ C07D

A new chemiluminescent seven membered cyclic peri
hydrazide and five of its biotin conjugates with various spacer groups are synthesized. The total framework of the chemiluminescent biotin conjugates is constructed taking advantage of a convergent synthesis from various stable intermediates employing DCC condensation and NHS activation.

N V KrishnaMurthy & A Ram Reddy*

2523

Synthesis and investigation of mass spectra of
3-substituted-2-thioxo-imidazolidin-4-one derivatives

IPC: Int.Cl.⁸ C07D

3-Substituted-2-thoxo-imidazolidin-4-one 2 is prepared via cyclization of compound 1 with ethyl chloroacetate in the presence of fused sodium acetate. The mass spectral fragmentation pattern of some of the prepared compounds are described.

M E Abd El-Fattah

2534

Synthesis and biological evaluation of ureido derivatives as VLA-4 antagonists

IPC:.Int.Cl.⁸ C07D

Synthesis of new compounds as VLA-4 antagonists based on bioisosteric replacements of ureido and amido moieties and their biological evaluation are reported.

V J Sattigeri*, A Soni, L K Gupta, A Ray, S Ahmad,
J B Gupta & M Salman

Notes

2542

N-Octyl quinolinium tribromide. A task specific quinoline based ionic liquid as a new brominating agent

IPC: Int.Cl.⁸ C07D

M P Kaushik*  & Vivek Polshettiwar

2546

Lewis acid promoted synthesis of 2(3H)-benzofuranones

IPC: Int.Cl.⁸ C07D

A Lewis acid promoted one-step synthesis of 2(3H)-benzofuranones via an intramolecular rearrangement of the corresponding substituted O-methoxyacetyl benzenes and coumarins is described.

B Ravindra Babu, Shilpika Bali, Rajeev Sakhuja & Subhash C Jain*

2549

A simple synthesis of a-methyl-g-keto acids

IPC: Int.Cl.⁸ C07C

Bharati Pawar & Pradip Lokhande*

2552

Oxidative regeneration of carbonyl compounds from their oximes using in situ generated superoxide

IPC: Int.Cl.⁸ C07C

Superoxide ion, generated in situ by the phase transfer reaction of potassium superoxide and 18-crown-6, brings about an easy oxidative regeneration of a variety of carbonyl compounds from their oximes under significantly mild reaction conditions at room temperature.

K N Singh*, Jyotsna Pandey & Manorama Singh

2556

Bioactive diterpenes from the mangrove Avicennia officinalis Linn

IPC: Int.Cl.⁸ A61K

From the hexane and ethyl acetate extracts of A. officinalis, known diterpenes including rhizophorin-B 1 and a new diterpene 2 have been isolated and their antimicrobial activities have been evaluated.

C Subrahmanyam, S Ratna Kumar &

G Damodar Reddy

2558

Synthesis, insecticidal and antimicrobial activities of some heterocyclic derivatives of quinazolinone

IPC: Int.Cl.⁸ C07D

Some new 4-phenyl-2,3-dihydro-6-(substitutedaminoethyl)-10-iodo[1,2,4]-triazino[2,3-c]-quina-zolin-5-ones 6-14 have been synthesized from 4-(phenyl-2,3-dihydro-6-methyl-10-iodo [1,2,4]-triazino[2,3-c]quinazolin-5-one 5 by introducing different heterocyclic nuclei. Compounds 5 and 6-14 have been screened for insecticidal, anti-fungal and antibacterial activities. Compound 4-phenyl-2,3-dihydro-6-(b-naphthyl-aminoethyl)-10-iodo[1,2,4]-triazino[2,3-c]-quinazolin-5-one 14
has been found to be the most potent compound of the present study which shows mortality of insects at 190.6 min while standard compounds exhibit at 280 min at a concentration of 5 g/L. Moreover, this compound also possesses anti-bacterial activity. The structure of these compounds have been elucidated by IR, ¹H NMR, mass spectroscopy and elemental analysis.

6 - 14

Tripti Singh*, Shalabh Sharma,
Virendra Kishore Srivastava & Ashok Kumar

2566

Chemical study on Garhwal Himalayan Lichen Usnea emidottertis

IPC: Int.Cl.⁸ C07C

Usnea species are medicinally important species so we take unexplored, Usnea emidotteris. Seven components 2- hydroxy-3-methoxy-4,6-dimethyl ethyl benzoate, 2,4-dihydroxy-3,6-dimethyl ethyl benzoate, 2-hydroxy-4-methoxy-3,6-dimethylbezoic acid, usnic acid, barbatic acid, diffractaic acid and evernic acid are isolated first time from Usnea emidotteries and identified from their physicochemical data.

4                                                                                                  5

6                                                                                               7

M S M Rawat*, Vertika Shukla, Sandeep Negi & G Pant

2571

Microwave induced, solvent-free Knoevenagel condensation of 4-oxo-(4H)-1-benzopyran-3-carbaldehyde with Meldrum’s acid using alumina support

IPC: Int.Cl.⁸ C07D

A rapid, solvent-free and environmentally friendly Knoevenagel condensation reaction of 4-oxo-(4H)-1-benzopyran-3-carbaldehyde 1 with Meldrum’s acid 2 has been carried out under microwave irradiation by using acidic alumina support.

S S Shindalkar, B R Madje & M S Shingare*

2574

Isolation of chalkones from the seeds of Psoralea corylifolia Linn.

IPC: Int.Cl.⁸ A61K

Isolation and characterization of a new chalkone namely 4,2’–dihydroxy–2’’–(1’’’–methyl ethyl)–2’’–3’’–dihydro–(4’’,5’’,3’,4’) furano chalkone 1 along with a known chalkone 4,2’–dihydroxy–4’–methoxy–5’–(3’’’,3’’’–dimethyl allyl)–chalkone 2 have been carried out from the seeds of the desert variety of Psoralea corylifolia Linn.

Deepshikha Agarwal, S P Garg & Pramilla Sah*

2580

Correlation between the pKa and pharmacological properties of some imidazolin–5(4H)-ones, their precursors and Schiff’s bases

IPC: Int.Cl.⁸ C07D

The pKa value of some synthesized imidazolin-5(4H)-ones and their precursors, Schiff’s bases are determined by potentiometric method and the analgesic activity and CNS depressant property are evaluated, which are correlated with the pKa values. It is found that a correlation is established in best fit curve of 3^rd order polynomial equation.

J K Gupta, Biplab De* & V S  Saravanan

Authors for correspondence are indicated by (*)

IPC: International Patent Classification

Int.Cl⁸.: International Classification, 8th Edition, 2006