Indian Journal of Chemistry

Sect. B: Organic Chemistry including Medicinal Chemistry

Total visitors: 2,640  since 11-11-05

VOLUME 44 B

NUMBER 11

NOVEMBER  2005



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 Km 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