Indian Journal of Chemistry

Sect. B: Organic Chemistry including Medicinal Chemistry

CONTENT

Papers

2295

7-[(4-Substituted phenyl-piperazin-1-yl)-alkoxyl]-4-methylchromene-2-ones as potential atypical antipsychotics: Synthesis and pharmacological evaluation

IPC: Int.Cl.⁷ C 07 D // A 61 P/28

7-Hydroxy-4-methylchromene-2-one and arylpipera­zines have been linked by alkoxy chain and the resulting title compounds have been screened for their atypical antipsychotic activity.

S M Shelke, Sushilkumar, Nitin Sati, V S Veer,

S H Bhosale*, S L Bodhankar, K R Mahadik &

S S Kadam

2301

Synthesis and preliminary anticancer activity of new 1H-4,5-dihydro-3-(3-hydroxy-2-naphthyl)-4-substituted-1,2,4-triazoline-5-thiones. Part II

IPC: Int.Cl.⁷ C 07 D // A 61 P 35/02

Some 1,2,4-triazoline-5-thiones have been synthe­sised in two steps. In the first step thiosemicarbazides 1g-k are prepared from 3-hydroxy-3-naphthoic acid hydrazide and appropriate isothiocyanates, and in the the second step 1H-4,5-dihydro-3-(3-hydroxy-2-naphthyl)-4-substituted-1,2,4-tri­azoline-5-thiones 2g-k are prepared from thiosemicarbazides. Four compounds have been evaluated in vitro for their primary cytotoxicity.

H Nese Dogan, Arzu Duran & Sevim Rollas*

2308

Pro-drug of forskolin and its 2-hydroxyacyl analogues^†

IPC: Int.Cl.⁷ C 07 C

Synthesis of water soluble pro-drug of forskolin and its novel 2-hydroxy-acyl derivatives having specificity towards positive inotropic activity is reported. However, these compounds do not show in vivo activity.

Bansi Lal*, Ashok Kumar Gangopadhyay, Ramanujam Rajagopalan & Anil V Ghate

2314

Stereoselective synthesis of the enantiomer of the fatty acid component of the potent immuno­suppressant, stevastelin

IPC: Int.Cl.⁷ C 07 C, C 07 D // A 61 P 37/06

A novel, stereoselective synthesis of the enantiomeric fatty acid fragment of stevastelin is described.

Sadagopan Raghavan*, S Ramakrishna Reddy & B Rajitha

2322

Kinetic study on lipase-catalyzed esterification in organic solvents

IPC: Int.Cl.⁷ C 07 C

A twin inhibition is observed for the esterification reaction between ethanol and isovaleric acid using immobilized lipase from Rhizomucor miehei in hexane and in mixed solvent system. The observed bi-substrate inhibition pattern follows a Ping-Pong Bi-Bi mechanism with dead-end inhibition of enzyme by both the substrates. An increase in K_m value for alcohol in mixed solvent (0.645 M) than in hexane (0.256 M), indicates that the enhanced solvation of ethanol in mixed solvent results in lower degree of inhibition.

G V Chowdary & S G Prapulla

2328

Microwave irradiated high-speed solution synthesis of peptide acids employing Fmoc-amino acid pentafluorophenyl esters as coupling agents

IPC: Int.Cl.⁷ C 07 K

A solution phase synthesis of peptide acids employing commercially available Fmoc-amino acid pentafluorophenyl esters as coupling agents under microwave irradiation has been demonstrated. The coupling has been found to be fast and completed in 30-45 sec. The resulting N-protected peptide acids are obtained in good yield as well as purity.

Vommina V Suresh Babu* & R V Ramana Rao

2333

On the regiospecificity of 3,5-disubstituted pyrazoles derived from C-acylated-b-enamino­nitriles and esters

IPC: Int.Cl.⁷ C 07 D

Direct and unambiguous evidences are provided in support of the regiospecifity of 3,5-disubstituted pyrazoles derived from a-acyl-b-enaminonitriles  and esters.

A Mukherjee, M Mishra, A Chatterjee,

M Sarkar, S K Dutta Chowdhury &

Kumar K Mahalanabis*

2338

Regioselective one-pot synthesis of 3,5-diaryl­pyrazoles

IPC: Int.Cl.⁷ C 07 D

One-pot synthesis of 3,5-diarylpyrazole has been reported with environmentally friendly molecular iodine and the comparative regioselectivity of pyrazoles obtained via pyrazolines and flavones is studied.

P D Lokhande^*, B Y Waghamare & S S Sakate

2343

Synthesis and antihypertensive activity of new 1,4-dihydropyridines

IPC: Int.Cl.⁷ C 07 D//A 61 P  9/12

Various dihydropyridines in which o-nitrophenyl group of nifedipine has been replaced with 2-alkylthio-1-benzyl-5-imidazolyl substituent and the 2-position of dihydropyridine has been substituted with 2-(1-imidazolyl)ethyl or 2-(2-dimethylamino)- ethyl have been synthesized and tested as antihypertensive agents in rats. All of them have been found to be less effective than nifedipine.

Farzin Hadizadeh*, Zahra Fatehi-Hassanabad, Mohammad Bamshad, Hamed Poorsoghat &

 Mohammad Fatehi-Hassanabad

2348

Synthesis and characterization of organotin (IV) complexes; monoalkyltin (IV) pyridine­carboxy­lates

IPC: Int.Cl.⁷ C 07 D

Reactions of monoalkyltin(IV) trichloride with sodium salts of pyridinecarboxylic acid in 1:3 stoichiometry yields complexes of the type RSn(O₂CPy)₃ (R=PhCH₂, 2-ClC₆H₄CH₂, 4-ClC₆H₄CH₂, Py=2-pyridinyl, 3-pyridinyl, 4-pyridinyl). All the complexes have been characterized by elemental analyses, IR and ¹H, ¹³C and ¹¹⁹Sn NMR spectroscopy. The crystal structure of monobenzyltin(IV) 2-pyridinecarboxylate has been determined by single crystal X-ray diffraction. In this complex, the central tin atom is rendered seven-coordinate in a distorted pentagonal bipyramidal geometry.

Handong Yin*, Gang Li & Hao Long Xu

2355

Synthesis of some antimicrobial heterocycles from pyranotetrahydrocarbazole

IPC: Int.Cl.⁷ C 07 D

Facile synthesis of 1 and its Pechmann condensation with various acyclic, cyclic, aromatic heterocyclic b-keto esters to afford 2-4 and with malonic acid to yield 5 as also its reaction with isatin and malononitrile to yield 6 has been described.

Vinata V Mulwad* & Chetan A Patil

2362

Chemical constituents of Mussaenda incana

IPC: Int.Cl.⁷ A 61 K 35/00

The isolation of shanzhilactone 1 along with mussaenoside, barlerin, lupeol and b-d-glucose from the stem of Mussaenda incana is reported.

Biswanath Dinda*, Sudhan Debnath, Santanu Majumder, Shiho Arima, Nariko Sato & Yoshihiro Harigaya

2367

Thienopyrimidines as hetryl moiety in 2-azetidi­nones: Synthesis of 4-hetryl-2-azetidinones

IPC: Int.Cl.⁷ C 07 D

Some 4-hetryl substituted b-lactams have been prepared from appropriately substituted thieno­pyrimidone derivatives.

Seema Kanwar & S D Sharma*

Notes

2372

Two new aliphatic compounds from Cassia fistula L.

IPC: Int.Cl.⁷ C 07 C // A 61 K 35/00

cis-Heptacosanyl-5-hydroxypentadec-2-enoate 1 and octacosan-5, 8-diol 2 have been isolated from the leaves of Cassia fistula. Their structures have been elucidated by chemical and spectral studies.

1

2

R S Singh*, H Singh, H S Pandey, R P Pandey &
Sheela Singh

2375

Synthesis, characterization and antimicrobial activities of fused 1,6-naphthyridines

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

An easy two-step synthesis of fused naphthyridines has been arrived from 3-formylquinolin-2(1H)-one with aryl amines which underwent condensation and cyclization by PPA conditions. All the synthesized compounds have been screened for their antibacterial and antifungal activities.

T Suresh, T Dhanabal, R Nandha Kumar &

P S Mohan*

2380

Synthesis of substituted benzo[e,f]-s-indaceno[2,3-d]­­pyrazoles

IPC: Int.Cl.⁷ C 07 D

Ethyl-9-oxo-7-phenyl-4,5,7,8-tetrahydro-9H-benzo-[e,f] s-indaceno-8-glyxolate 3 on treatment with hydrazine hydrate, semicarbazide hydrochloride and thiosemicarbazide hydrochloride yields 3-carbethoxy-6,7-dihydro-4-phenyl-l,4H-benzo[e,f] s-indaceno- [2,3-d] pyrazole 4, 1-carbamido-3-carbethoxy-6,7-dihydro-4-phenyl-lH, 4H-benzo [e,f]-s indaceno-[2, 3-d] pyrazole 5 and 3-carbethoxy-6,7-dihydro-4-phenyl-lH,4H-thiacarbamidobenzo[e,f]-s-indaceno [2,3-d] pyrazole 6 respectively. The structures of these compounds have been confirmed from their ¹H NMR spectra.

Sharda Goel

2383

CaCl₂.2H₂O assisted oxidation of alcohols with (NH₄)₂Cr₂O₇

IPC: Int.Cl.⁷ C 07 C 39/00

CaCl₂.2H₂O has been found to be an efficient  reagent for the acceleration of the oxidation of  alcohols to their corresponding carbonyl compounds with (NH₄)₂Cr₂O₇ in solution and under solvent free conditions.

F Shirini*, M A Zolfigol & A Safari

2387

Bismuth oxide perchlorate as a highly efficient and chemoselective catalyst for thioacetalization of carbonyl compounds under solvent-free conditions

IPC: Int.Cl.⁷ C 07 D

Bismuth oxide perchlorate efficiently and chemo­selectively catalyzes the thioacetalization of both aliphatic and aromatic carbonyl compounds 2 under solvent-free conditions to give 1a-k.

B Sunil Kumar, Y Thirupathi Reddy,

P Narsimha Reddy, G V P Rao & (Ms) B Rajitha*

2390

Isolation and identification of fatty acids from berries of sea buckthorn (Hippophae rhamnoides)

IPC: Int.Cl.⁷ A 61 K 35/00

Five fatty acids, (2-hydroxydecanoic acid, nona-7-enoic acid, undec-9-en-7-ynoic acid, 13-phenyl­tridecanoic acid and 5, 9, 21-nonacosatrienoic acid) have been isolated and characterized from the ethanol extract of the sea buckthorn berries (Hippophae rhamnoides). The structure of new fatty acid namely, undec-9-en-7-ynoic acid (AS-3) has been elucidated by the spectroscopic techniques.

Anand Kumar Singh, Manisha Nivsarkar,

B N Acharya & M P Kaushik*

2393

Efficient synthesis of bis(indolyl)methanes catalyzed by TiCl₄

IPC: Int.Cl.⁷ C 07 D

TiCl₄ is found to be an efficient catalyst for the electrophilic substitution reaction of indoles with aromatic aldehydes in dichloromethane to afford the corresponding bis(indolyl)methanes 3a-k at ambient temperature.

Y Thirupathi Reddy, P Narsimha Reddy,

B Sunil Kumar & (Ms) B Rajitha*

2396

A mild and efficient method for tetrahydro­pyranylation and detetra­hydro­pyranylation of alcohols and phenols by BiOClO₄.xH₂O (or) BiONO₃

IPC: Int.Cl.⁷ C 07 C, C 07 D

BiOClO₄.xH₂O (or) BiONO₃ have been found to be efficient catalysts for the tetrahydro pyranylation and detetrahydropyranylation of different alcohols and phenols 3a-k rapidly in high yields at room temperature.

Y Thirupathi Reddy, P Narsimha Reddy,

B Sunil Kumar, N Srinivasulu & (Ms) B Rajitha*

2399

Chemical constituents of Rodgersia sambucifolia Hemsl

IPC: Int.Cl.⁷ A 61 K

Two new lignan diglycosides, hypophyllanthin-2a-O-β-apiofuranosyl-(1→6)-O-β-glucopyranoside 1 and 8-methoxyhypophyllanthin-2a-O-β-apiofuranosyl-(1→6)-O-β- glucopyranoside 2 have been isolated from the ethanol extract of the roots of Rodgersia sambucifolia Hemsl and their structures have been elucidated on the basis of spectral data and chemical studies.

1   R₁=Apiose  R₂=H

2   R₁=Apiose  R₂= OMe

Hao-bin Hu, Shang-zhen Zheng*

Xu-dong Zheng & Xu-wei Shen

2404

Synthesis and antidiabetic activity of 2-amino [5¢(4-sulphonylbenzylidine)-2,4-thiazolidinedione]-7-chloro-6-fluorobenzothiazole

IPC: Int.Cl.⁷ C 07 D // A 61 P

S R Pattan*, Ch Suresh, V D Pujar, V V K Reddy,
V P Rasal & B C Koti

2409

Ceric ammonium nitrate catalyzed efficient and chemoselective method for protection and deprotection of 4-oxo-4H-1-benzopyran-3-carbaldehydes

IPC: Int.Cl.⁷ C 07 D

A chemoselective, mild and efficient method for the synthesis of acylals and their deprotection to 4-oxo-4H-1-benzopyran-3-carbaldehydes catalyzed by ceric ammonium nitrate (CAN) are carried out in good yields and all compounds are characterized by spectral data.

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

2412

A direct single step synthesis of 1,3-diaryl-4-cyanopyrazoles and their conversion to 1,3-diaryl-4-(4,6-diamino-1,3,5-triazin-2-yl)pyrazoles

IPC: Int.Cl.⁷ C 07 D

A series of 1,3-diaryl-4-(4,6-diamino-1,3,5-triazin-2-yl)-pyra­zoles 6a-g have been synthesized. 1,3-Diaryl-4-cyanopyrazoles 5a-i required as intermediates have been prepared in a single step from acetopheonone hydrazones 4a-i.

G Jagath Reddy*, D Manjula & K Srinivasa Rao, Md Khalilullah & D Latha

2416

Additions and Deletions

Announcements

2417

Second International Symposium On Green/ Sustainable Chemistry

Authors for correspondence are indicated by (*)

IPC: International Patent Classification

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