Indian Journal of Chemi stry Vol. 438 , February 2004, pp. 399-405

Synthesis and biological activity of 4-oxothiazolidines and their 5-arylidenes

S K Srivastava*, R Yadav & S D Srivastava

Synthct ic Organi c Chcmistry Laboratory , Chcmi stry Departmcnt. Dr H S Gour Uni vcrs ity. Sagar 470003, India

Recei l'ed <'I October 2002; (Il 'cepted (revised) 28 Allgllst 2003

A scri es of 5-arylidcnc-2-aryl-3-1 (2-benzothi azo lylthio)-acelamidyll-1 ,3-thi azolid in -4-ones have bcen synthesised by appropriate methods. All thc compounds have becn scrcencd for thcir antifungal ac ti vity aga inst Calldida a/bicoll s, FII .I'a­rilllll heterosporilllll and Aspergillus lIiger , anti bacteri al ac ti vity aga inst Bacilllls slibs/ ilis, Sa/Illollella typhilllllrilllll and Es­cherchia coli, and anti innammatory act ivity against the ea rragecnan induced rat paw oedema in albino rat s and anthclmintic ac ti vi ty against the expcrimcntal infec tion of AllcyciosfOllla cey/alliclIlII and HYlllello/epsis lIalla in rats. In the primary serecning. some of the compounds exh ibit apprec iable acti vity. Thc strueturcs of thc sy nthcsised compounds (4 and 5) have bccn cstabli shcd on the basis of their clcmental analyscs and spectral data .

IPC: Int.CL7 C 07 0277/00 II A 61 P 31/04, 33/10, 1106

2-Mercaptobenzothi azole deri vatives are known to possess various biological acti vities t

-9

, 4-Thiazolidi­nones are also well known for versatil e pharma­cological acti viti es to- t3 such as hypnotic , anaesthetic, anti fu ngal, anthelmintic, antiviral , CNS stimulant etc. The incorporation of 4-oxothi azolidine and 5-ary lidene moiety in 2-mercaptobenzothi azo le frame­work has been found to enhance the act ivity. Hence, in present study the 2nd position in 2-mercapto­benzothiazole moiety hav ing thi ol (-SH) group, was used as the target fo r chemical change (Scheme I). These observations promoted us to sy nthesise the tit led compounds (1-5) as per Scheme I with a view to evaluate their antimicrobial , antiinflammatory and anthelmintic efficacy.

Condensation of 2-mercaptobenzothiazo le with ethylchloroacetate in dry acetone gave ethyl-2-(benzothiazolylthio)-acetate 1. The compound 1 on ammonolys is with hydrazine hydr:1te in ethanol yielded [2-(benzothi azolylthio)-acetyll hyd raz ine 2. Compound 2 underwent condensation with different carbonyls to afford the arylidene [2-(benzolhiazo lyl­thi o)acetami dy l] 3, Thcse intermediates on cyc lo­addition with mercaptoacetic ac id yielded fivc membered heterocyc lic derivatives 2-aryl-3- [(2-benzothiazol ylthi o )-acetamidyl]-l , 3-thi azol idi n-4-ones 4, Compound 4 on reaction with vari ous carbonyls usin g sodium ethoxide in ethanol furni shed 5 -ary Ii dene-2 -ary 1-3- [(2 -benzoth i azo l y I th i 0 )-accta­midyl]- ] ,3-thiazol idin-4-ones 5 (Table I ). All the compounds synthesised were adequately charac teri sed by their elemental anal yses and spectral IR and NMR data.

a N

I }-SH

~ S

~ CICH,COOC, H,

I }-SCH,COOC,H, a N

~ S

1

~ NH,NH,

Scheme I

400 INDIAN J. CHEM., SEC B, FEBRUARY 2004

Table I - Characterisation data of compounds 3b-n, 4b-n and Sb-n

Compd RI R2 R) R4 Yield Mp Mol. Found (%) (Calcd)

(%) °C formula C H N

3b H 2,4-(N02)2C6HJ 60 203-04 CI6HIINsOSS2 46. 01 2.59 16.70 (46.04 2.63 16.78)

3c H 3-CIC6H4 77 12 1-23 CI6HI 2N)OS2C I 53 .11 3.3 1 11 .60 (53 .1 S 3.32 11 .63)

3d H 2-B rC6H4 73 111-13 CI6HI 2N30S2Br 47 .22 2.94 10.35 (47.29 2.95 10.34)

3e H 3-BrC6H4 70 117-1 9 CI6HI 2Np S2Br 47 .27 2 .90 10.31 (47 .29 2.95 10.34)

3f H 4-BrC6H4 70 145-47 CI6HI2N30S2Br 47 .26 2.89 10.3 1 (47 .29 2.95 10.34)

3g H 2-0CH)C6H4 65 176-77 C17HIsN302S2 57 .10 4. 15 11.71 (57. 1 4.20 11.76)

3h H 3,4,5-(OCH3) 3C6H2 55 183-85 CI 9HI 9N304S2 54.62 4.5 1 10.00 (54.67 4.55 10.07)

3i H 2-0HC6H4 50 100-02 C1 6HI )N302S2 55 .95 3.70 12.21 (55.97 3.79 12.24)

3j H 3-0HC61-14 52 109-10 C I6H1)N)0 2S2 5593 3.73 12.22 (55.97 3.79 12.24)

3k H 4-0HC6H4 56 117- 19 C I6H 13N)02S2 55 .9 1 3.72 12.20 (55.97 3.79 12.24)

31 C H) 4-CIC6H4 68 19 1-93 C I7 H 14N30S2Cl 54.33 3.70 11.l7 (54 .40 3.73 11 .20)

31ll CH) 4-0CH3C6H4 60 186-87 C 1sH17N)0 2S2 58 .19 4.5 1 11 .28 (58 .22 4.58 11 .32)

3n CH3 4-0HC6H4 58 205 -07 CI7HI SN30 2S2 57.99 4.13 11.72 (57.I L 4 .20 11.76)

4b H 2,4-(N02)2C6H) 6 1 235 -37 C lsH I3 Ns06S) 4391 2.60 14.22 (43.99 2.64 14.25)

4c H 3-CIC6H4 76 24 1-43 CI8H I4 N30 2S)CI 4961 3.20 9.61 (49.65 3.21 9.65)

4d H 2-BrC6H4 7 1 149-51 Cl sH 14 N30 2S)Br 4498 2.89 8.70 (45.01 2.9 1 8.75)

4e H 3-BrC6H4 68 153-55 C lsH 14 N)0 2S)Br 4500 2.90 8.71 (45.0 1 2 .91 8.75)

4f H 4-B rC6H4 64 159-60 C IS H I4 N30 2S)Br 4500 2.93 8.70 (45.01 2.91 8.75 )

4g H 2-0CHJC6H4 68 190-9 1 C I9H I7N)O)S3 52.88 3.91 9.70 (52.90 3.94 9 .74)

4h H 3,4,5-(OCH3h C6H2 6 1 225-27 C2IHn NJOsS) 5 1 19 4.46 8.50 (51.21 4.47 8.53)

4i H 2-0HC6H4 58 121-23 C1 sH1 sN)OJS) 5693 3.90 11.00 (56. 99 3.95 11.08)

4j H 3-0HC6H4 55 135-36 Cl sH IsNJO)S.l 5698 3.93 11 .0 1 (56.99 3.95 11 .08)

4k H 4-0HC6H4 56 139-41 Cl sH IsNJO.lS) 56.92 3.90 II. 0 I (56.99 3.95 11 .08)

41 CHJ 4-CIC6H4 63 227-29 C Il) H 16NJ0 2SJCl 50 .71 3.53 9.34 (50.77 3.56 9.35)

4111 CH] 4-0CH]C(,H., 59 2 12- 13 C20 H Il)N .10 2S) 54 .15 3.81 9.45 (54.1 7 3.83 9.48)

-Col/ ld

SR IV ASTA V A et al.: SYNTHESIS OF 4-0XOTHIAZOLlDIN ES 401

Table I - Characteri sati on data of compounds 3b-n, 4b-n and 5b-n--Contd

Compd RI

4n

5b

5c

5d

5e

Sf'

5g

5h

5i

5j

5k

51 C H, 4-C IC6H.,

5m

5n

Biological Activity Antimicrobial activity. The compou nds 4a-n and

5a-n were screened for their antibacteri al act ivity against Bacilllls slIbs/ilis, Sallllonella /ypherilllll and Escherichia coli at 50 and 100 ppm concentrations and antifunga l activ ity agai nst Calldida albicans, FlIsariul1I he/erosporiw1/ and Aspergilllls niger at 10, 50 and 100 ppm concentrations by filter paper disc technique '-l·

15. Standard antibacterial Streptomycin

and anti funga l Griseoful vin were also tes ted under similar conditions for comparison. Results are presented in Tables II and III .

Antiinflammatory activity . The compounds 4a-n and 5a-n were also tested for their ant ii nflammatory acti vity uSIng carrageenan induced 111 rats paw oedema method of Winter e/ al. I ii at an oral dose of 50 mg/kg b. w. in alb ino rats (weighing 80- 11 Og). The percent inhibition of innammati on was calcul ated by apply ing Newbould form ul a l 7

. Results are presented in Table IV.

Yield (%)

6 1

67

74

65

56

6 1

57

55

5 1

54

53

62

55

58

mp

°C Mol.

formula Found (%) (Calcd) C H N

201-03 52.88 3.90 (52.90 3.94

280-83 C2sH IsN70 IOS, 44.80 2. 19 (44.84 2.24

136-37 C2s HI7 N)0 2S, Ci2 53.83 3.00 (53.85 3.05

162-63 C2sH I7 N)0 2S3Br2 46.40 2.6 1 (46.43 2.63

166-67 C2sH I7 N)0 2S)Br2 46.4 1 2.62 (46.43 2.63

170-71 C2sH I7 N,0 2S3Br2 46.4 1 2.62 (46.43 2.63

2 11-1 2 C27Hn N)0 4S, 59.00 4. 13 (59 .0 1 4. 18

240-42 C" H31 N, OgS.1 55 .59 4.60 (55.60 4.63

14 1-41 C2s H1 9N304S) 57.53 3.60 (57.58 3.64

155-57 C2s H 19N.10 4S.1 57.50 3.62 (57.58 3.64

159-6 1 C2s H 19N,0 4S.1 57 .55 3.6 1 (57.58 3.64

249-5 1 C27 H2IN)0 2S,Ci2 55 .36 3.51 (55.38 3.58

225-27 C29H27 N.10 4S) 60.29 4.6 1 (60.3 1 4.67

2 13- 15 C27H23 N, 0 4S, 59.00 4. 16 (59.0 1 4. 18

9.72 9.74)

14.61 14.64)

7.5 1 7.54)

6.48 6.50)

6.46 6 .50)

6.49 6.50)

7.63 7.65)

6.20 6.27)

8.00 8.06)

8.05 8.06)

8.05 8.06)

7.1 2 7. 17)

7.25 7.27)

7.63 7.65)

Anthelmintic activity. The sy nthes ised com­pounds 4a-n and 5a-n were also screened against ex­perimental infection in Ancyclos/oll1a ceylalliculII in hamsters and HYl1l enolepsis nana in young male rates (weighing 30-40 g) at a dose of 250 mg/kg x 3 and

IX 250 mg/kg by the method of Steward . Mebendazole was used as a standard drug which killed 100% of A.

ceylaniculI1 at an ora l dose of 250 mg/kg x 3 and 100% worms were cleared up in H. /lalla infecti on at an oral dose of 250 mg/kg (Table V).

Experimental Section

Melting points were taken in open capillari es and are uncorrected . I R spectra were recorded on a Shimadzu 820 1 PC FTIR (u max In cm-\ and IH NMR spectra on a Brucker DRX-300 in CDCI, at 200 MH z using TMS as an internal standard . Purity of the compounds was checked by TLC on silica ge l pl ates .

402 IND IA N J. CHEM. , SEC B, FEBRUARY 2004

Table 11- Antibacterial acti vity data of compounds 4a-n and Sa-n

Compd B.slIbsliiis S.Iyph illlll ri 11111 E.coli 50 ppm 100 ppm 50 ppm 100 ppm 50 ppm 100 ppm

4a ++ + + ++

4b + + ++ + +

4c ++ ++ ++ +++ +++ +++

4d ++ +++ ++ ++ ++ -1 +

4e +++ +++ ++ ++ +++ +++

4f +++ +++ ++ +++ ++ +++

4g + ++ + + + ++

4h + + +

4i ++ ++ + ++ ++ ++

4j + + + ++ ++

4k + + + + + 41 + +

4111 + + + + +

4n + + + + ++

Sa + + + + +

Sb + + + ++ -1+

Sc ++ +++ ++ ++ ++ ++

Sd +++ +++ ++ +++ +++ +++

Se +++ ++++ ++ +++ +++ ++++

Sf +++ +++ +++ +++ +++ ++++

Sg + + + + ... Sh + .,. Si ++ ++ ++ ++ + ++

Sj + + + Sk + + + ++ + ++

51 + + + + ++

5111 + + + + ~-

Sn + + + + + .;-

SM +++ ++++ +++ ++++ +++ ++++

SM=Streptomyc in . inhibition diameter inmm:(-)<6, (+) 7-89, (++) 10.15 (+++) 16-22,(++++)23-28.

Ethyl 2-(-benzothiazolylthio) acetate 1. Equimo­lar so lution of 2-mereapto-benzothiazole (0.1 mo le) and ethy l chl oroacetate (0. 1 mole) in dry acetone (40 mL) in the presence of anhydrous K2C03 (5g) was refluxed on a water-bath for about 16 hr. The solvent WJS removed i ll vacuo and the residue was recrystal­li zed from chloroform to furnish compou nd I , yield

79%, mp 57-59°C. Anal. Calcd for C II HIIN02S2: C, 52. 18; H, 4.22 ; N, 5.40. Found: C , 52 . 17 ; H, 4 .20; N , 5.34%; IR: em-I, 3023, 1510, 11 05 , 1070, 1033,638 (aromatic ring), 1722 (>C=O of este r), 1615 (C=N), 1225 and 1044 (C-O-C), 720 (C-S-C) and 2910, 2870, 1425 and 7 15 (C H2 and CH3) ; IH NMR: 8, 1.25 (t,3 H, .I=7Hz, -COOCH2CH3) , 4 . 10 (q, 2H, .I=7Hz

COOCH2CHJ), 4.48 (s, 2H, S-CH2) and 6.70-7 .90 (m, 4H, Ar-H).

[(2-BenzothiazolyIthio) acetyl]-hydrazine 2. Ethy l (2-benzothi azo lylth io)acetate (0 . 1 mole) and hydrazine hydrate (0.1 mole) in methano l (30 mL) was refluxed for about 5 hr on a steam-bath . After cooling the .resulting solid was filte red, dri ed and re­crystalli zed from ethanol to get compound 2, yield 76%, mp 194 -95°C. Anal. Calcd for C9H9N30S2: C, 45.22; H, 3 .10; N, 17.60. Found: C , 45 .15 ; H, 3.0 I ; N, 17.49%; IR: cm· l

, 3355,3382 (-NHNH2) and 1661 (C=O of amide) ; IH NMR: 8 6.8~-7 .96 (m , 4H , aro­matic ring), 4.4 1 (s, 2H, NH2), 4 .85 (s,2 H,S-CH2) and 7.85 (s, I H ,-CONH).

SRIVASTA VA et al. : SYNTHESIS OF 4-0XOTHIAZOLlDlNES 403

Table III - Antifungal activity data of compounds 4a-o and Sa-o

Compd C.albicalls F.heterosporium A.niger

10 ppm 50 ppm 100 ppm 10 ppm 50 ppm 100 ppm 10 ppm 50 ppm 100 ppm

4a

4b

4c

4d

4e

4f

4g

4h

4i

4j

4k

41

4m

40

Sa

Sb

Sc

Sd

Se

Sf

Sg Sh

Si

Sj

Sk

51

Sm

So

GF

+

+

+

++

+++

+++

++

+

+ ++

+

+

+

++

++

++

+++

+

+

+

++

+

++

+

+

++

++

+++

+++

++

++

+

+

++

++

+

+

++

+

++

++

++

+++

++

++

+

+

++

+

+

+++

++

+

++

++

+++

+++

++

++

++

+

++

++

+ ++

++

++

++

++

+++

+++

++

++ ++

+

++

++ +

++

++++

++

++

++

++

+

++

+

+

+

+

+

+

++ ++

++

++

+

+

+

+ +++

+

++

+++

++

++

++

++

++

++

+

+

+ ++

++

+++

++

++

++

+ +

+ +

++

+ ++

+++

+

+

++

+++

+++

++

++

+++

++

+

++

++

+

++

+

++

++

+++

+++

++

++

++

++

+ ++

++

+ ++

++++

+

++

++

+

+

+

+

+

+

+

+

+

+

++

++

+

++

+

+

+

+

+

+++

+

+

++

++

++

++

+

++

+

+

+

+

+

+

++

++

+++

+++

++

++

++

++

+

+

++

+

+ +++

+

+

+++

++

+++

++

++

++

+

+

++

++

+

++

++

++

++

+++

+++

++

++

++

++

++

++

++

+

++

++++

GF = Griesofulvin inhibition diameter in mm:(-)< 8,. (+) 9-11, (++) 12- 17, (+++)18-23, (++++),23-28

Arylidene-[ (2-benzothiazolylthio) acetamidyl 3. A mixture of compound 2 (0.003 mole) and 3-nitrobenzaldehyde (0.003 mole) and 2-3 drops of gl. acetic acid in ethanol (25 mL) was refluxed on a water-bath for about 6 hr. The solvent was removed and residue was recrystallised from chloroform methanol mixture to get compound 3, yield 79%, mp 151-52°e. Anal. Calcd for C1 6H1 2N40 3S2: C,51.50; H,3.16; N, 14.91. Found: C, 51.45; H, 3.11; N, 14.90%; IR: cm,l, 3342 and 1339 (-NH-), 1665 (>C=O), 1625 (-N=CH-); IH NMR: 8,4.45 (lH, s, N=CH), 8.15 (lH,s,CONH), 6.90 -7.70 (m, 4H, aromatic ring).

Likewise other compounds 3b-n were prepared by treating 2 with various aromatic carbonyls.

2-(3-Nitrophcnyl)-3-[ (2-benzothiazolylthio )-acet­amidyl]-4-oxo-thiazolidine 4. A mixture of 3a (0.01 mole) in ethanol and mercaptoacetic acid (0.01 mole) with a pinch of ZnCh was refluxed on a steam-bath for about 8 hr. The separated solid was crystallized from methanol to give compound 4a, yield 75%, mp 163-64°e. Anal. Calcd for ClsH14N404S3: C, 48.43; H, 3.13; N, 12.55; Found: C, 47.97; H, 2.97; N, 12.41%; IR: cm'l, 3342 and 1335 (-NH-), 1668 (>C=O amidyl), 1715 (C = 0, cyclic). 1342 (Ar-N02) iH NMR: 8, 8.55 (s,lH,-CONH-) 7.00-7.95 (m, 8H,

404 INDIAN 1. CHEM. , SEC B, FEBRUARY 2004

Table IV - Anti infl ammatory activity data of compounds 4a-n and Sa-n

Cornpd

4a

4b

4c

4d

4e

4f

4g

4h

4i

4j

4k

41

4111

4n

Sa

Sb

Sc

Sd

Se

Sf

Sg

Sh

Si

Sj

Sk

51

Sm

Sn

Volume of paw (rnL) after drug

admini stration (mean±SE)

o hr 5 hr

Total Percent increase inhibition in paw volu me

after

0.63±0.02 0.95± 0.02 0.32±0.0 I

0.59± 0.0 I 0.92± 0.03 0.33± 0.02

0.76±0.03 0.86± 0.03 0.20± 0.02

0.63± 0.02 0.88± 0.03 0.25± 0.02

0.65± 0.04 0.89± 0.02 0.24± 0.0 I

0.59± 0.0 I 0.85± 0.03 0.26± 0.02

0.66± 0.03 0.96± 0.03 0.30± 0.02

0.64± 0.03 0.96± 0.0 I 0.32± 0.03

0.58± 0.03 0.92± 0.02 0.34± 0.01

0.60± 0.02 0.94± 0.03 0.34± 0.03

0.6 1 ± 0.04 0.96± 0.03 0.35± 0.02

0.65± 0.0 1 0.98± 0.03 0.33± 0.02

0.50± 0.02 0.86± 0.02 0.36± 0.01

0.55± 0.02 0.90± 0.03 0.35± 0.03

0.53± 0.0 1 0.86±0.03 0.33± 0.02

0.56± 0.02 0.92± 0.04 0.36± 0.02

0.68± 0.03 0.90± 0.02 0.22± 0.01

0.50± 0.03 0.76± 0.02 0.26± 0.02

0.69± 0.02 0.86± 0.03 0.27± 0.02

0.60± 0.04 0.89± 0.02 0.29± 0.0 I

0.56± 0.02 0.92± 0.03 0.36± 0.03

0.54± 0.03 0.89± 0.02 0.35± 0.01

0.52± 0.03 0.87± 0.03 0.35± 0.02

0.63± 0.02 0.94± 0.02 0.3 1 ± 0.03

0.60± 0.04 0.93± 0.02 0.33± 0.0 I

0.57± 0.02 0.79± 0.02 0.22± 0.03

0.52± 0.03 0.85± 0.03 0.33± 0.02

0.61± 0.03 0.89± 0.02 0.28± 0.02

Phenyl 0.75± 0.02 0.9 1 ± 0.02 0. 16± 0.03

11.11

8.33

44.44

30.55

33.33

27.77

16.67

11.11

5.55

5.55

2.77

8.33

0.00

2.77

8.33

0.00

38.88

27.77

25. 10

19.44

0.00

2.77

2.77

13.88

8.33

38.88

8.33

22.22

55.55 -butazone

Control 0.62±0.02 0.98±0.03 0.36±0.02

Ar-H), 3. 18 (s ,lH ,-N=CH-) 3.60 (s ,2H,CH2) (cyclic) and 4.48 (s, 2H, S-CH2)'

Other compounds 4b-n were prepared in the si milar way using 3b-n respectively. Characterisation data are presented in Table I.

2-(3-N itrophenyl)-3-[ (2-benzothiazoly Ithio )-acet­amidyl]-5-(3-nitrobenzylidene)-4-oxo-thiazolidine 5. Equimolar solution of 4a (0.00 1 mole) and 3-nitrobenzaldehyde (0.001 mole) in dioxane in the presence of C2HsONa was refluxed for about 4 hr on a

Table V- Anthelmintic act ivi ty data of compounds 4a-n and Sa-n

Compd

4a

4b

4c

4d

4e

4f

4g

4h

4i

4j

4k

41

4m

4n

Sa

Sb

Sc

Sd

Se

Sf

Sg

Sh

Si

Sj

Sk

51

Sm

Sn

MD

A.ceylal/icum Dose % worm mg/kg reducti on

250 x 3 00

250 x 3 20

250 x 3

250 x 3

250 x 3

250 x 3

250 x 3

250 x 3

250 x 3

250 x 3

250 x 3

250 x 3

250 x 3

250 x 3

250 x 3

250 x 3

250 x 3

250 x 3

250 x 3

250 x 3

250 x 3

250 x 3

250 x 3

250 x 3

250 x 3

250 x 3

250 x 3

250 x 3

250 x 3

30

60

65

70

75

60

10

20

20

00

40

00

00

10

40

65

60

70

80

65

10

20

20

65

30

45

100

Ii.nana Dose Acti vel mg/kg Inac ti ve

250 x I

250 x I

250 x I

250 x I

250 x I

250 x I

250 x I

250 x I

250 x I

250 x I

250 x I

250 x I

250 x I

250 x I

250 x I

250 x I

250 x I

250 x I

250 x I

250 x I

250 x I

250 x I

250 x I

250 x I

250 x I

250 x I

250 x I

250 x I

250 x I

Inactive

Inacti ve

Inac ti ve

Acti ve

Acti ve

Acti ve*

Active*

Acti ve

Inactive

Inacti ve

Inacti ve

Inac ti ve

Inactive

Inac ti ve

Inactive

Inac ti ve

Inactive

Active

Active

Act ive*

Act ive*

Acti ve

Inac ti ve

Inacti ve

Inacti ve

Acti ve

Inactive

Inact ive

Active*

* The acti ve denotes 100% removal of the tapeworm alongwith their scolices.

steam-bath and the solvent was removed in vacuo. The resulting solid was recrystallised from ethanol to give compound 5, yie ld 55%, mp 201-02°C. Anal. Calcd for C2sHI7Ns0 6S3: C, 51.81 ; H, 2.93; N, 12.08. Found: C,5 1.75; H, 2.85 ; N, 12.00%; IR: cm", 3345 and 1330 (-NH-), 1710 (>C=O, cyclic), 1660 (>C=O: amidyl) , 1 622(>C=CHAr). 'H NMR : 8, 3.25 (s, IH ,­CHN), 6.99-7.10 (m,12H,ArNH), 4.45 (2H,S-CH2),

8.62 (s, IH,CONH) and 5.18 (s, lH,>C=CHAr).

SRIV ASTA V A et 01.: SYNTHESIS OF 4-0XOTHIAZOLIDINES 405

Other compounds Sb-n were synthesised similarly from 4b-n respectively. Characterisation data are presented in Table I.

Acknowledgement The authors are thankful to RSlC, CDRI, Lucknow

for providing spectral and analytical data of the compounds. Authors are also thankful to the Head of Botany Department of Dr H S Gour University , Sagar for biological screening.

References I Patil V H & Ingle D B, J Indian Cliem Soc, LVI, 1979, 1243. 2 Desai P S & Desai K R. J Indian Chem Soc, 71. 1994, 155. 3 Guru N & Srivastava S D, J scient ind Res, 60, 2001 , 601. 4 Rani B R, Bhalerao U T & Rahman M F, Indian J Chem,

29B, 1990, 995. 5 Singh S P & Vaid R K, Indian J Cliem , 25B, 1986, 288.

6 Chande M S & Jathar K S, Indian J Chem, 34B, 1995, 654. 7 Husain M I & Kumar V, Indian J Chefl/, 31 B, 1992, 673. 8 Jain R & Dixit A, J Indian Chem Soc, 67, 1990, 179. 9 Sawhney S N, Sharma P K & Gupta A, Indian J Chem, 32B,

1993, 1190. 10 Lodhi R S & Srivastava S D, Indian J Chem, 36B, 1997,

947 . II Mishra M, Srivastava S K & Shrivastava S D, Indian J

Chem, 36B, 1997, 826. 12 Srivastava S K, Srivastava S D & Srivastava So my a, Indian J

Cliem, 2002 (in Press). 13 Jaish L & S K Srivastava, J scient ind Res, 60, 2001 , 33. 14 Bayer A W, Kirba W W M, Shrries J L & Turk M, Am J Cli

Path, 45, 1966, 493 . 15 Vincent J G & Vincent H W, Proc Soc Exptl Bioi Med, 55,

1955, 112. 16 Winter C A, Risley E A & Nuss G W, Proc Soc Exptl Bioi, 3,

1962,544. 17 Newbould B B, Brit J Pharmacal, 21. 1963, 157. 18 Steward J S, Parasitol, 45, 1955, 255.