The Chemistry of Samandarine Model Compounds1 - Journal of

The Chemistry of Samandarine Model Compounds1. H. Franke, and R. Partch. J. Med. Chem. , 1966, 9 (4), pp 643–644. DOI: 10.1021/jm00322a062...
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NEW COUPOVSDS

July 1966

643

T LBLE I SOME

HYDRAZOSES O F 5-PHETYL-2,4-THI.~ZOLIDINEDIONE O=C-NH C,H,-CH

{

I

C=NN=R

S '' LIP, O C

R

----%

Yield,

%

Formula

C O S ( CeH:)N( CH,)C( CHd)=CCH=

259-260

90.02

C21H1&jOrS

CON(CeH;)N(CHa)C(CHa)=CNHCH=

254

56.00

CH~CH?OCHICH~NCH=

275 250

L

i

calcd----

H

C

found--H

7 %

S

C

S

62.21 4 . 7 2 17.28 62 52 4.90

17.01

C Z I H ~ O S ~ O ~59.99 S 4.80

19 99 59.42 5 07

20.10

18.32

Ci4Hi6?ia01S

38.00 5.50

14.50 57.81 4.94

14.79

38.40

C17Hd40Sa

57.95 3.43 15.90 57.20 3.98

15.81

antianemia, and antithyroid a c t i o i ~ - ~Some 5,5-dialkyl derivatives possess hypnotic properties.7-10 The methods for the preparation of both the parent compoiindll and many of its 12-15 Four new analogs derivatives are described iii literat~ire.~-~~s are listed in Table I.

tent neiirotoxic and convulsive activity in a "bteroidlike" molecrile, ~e iuidertook the synthezib aiid phy4ological evaluation of the heterocyclic portion of the alkaloid. K e suspected it to be responsible for the iiricommon activity.'

Experimental Section16 4-Formylantipyrine Hydrazone of 5-Phenyl-2,4-thiazolidinedione.-4-Antipyrine carboxylate (4.0 g, 0.02 mole) was dissolved in ethanol and made basic with NaOH. Thiosemicarbazide (1.8 g, 0.02 mole) was then added. After allowing the mixture t o stand for 10 min ethyl phenylchloroacetate (4.0 g, 0.02 mole) was added aiid the mixt'ure was shaken. Sodium acetate (1.6 g, 0.02 mole) and 6.0 ml of dilute acetic acid were then added and the mixture was refluxed for 30 min. Upon cooling a yellow crystalline solid was filtered off, air dried, and recrystallized from ethanol The hydrazones of S-formylaminoantipyrine, K-formylmorpholine, and 9-formylbenzythiazole Kere prepared and purified in the same manner. _

_

~

(3) E. V. Vladeimirskaya, N . AI. Turkevich, Zh. Obshch. K h i m . , 26, 2150 (1955); Chem. Abstr., 60, 8605b (1956). (4) S . XI. Turkerich, E. V. Vladsimirskaya, Z h . Obshch. K h i m . , 24, 2010 (1954); Chem. Abstr., 49, 14737i (1955). (5) 3. M . Kapustyak, Farm. Zh., 14, No. 3, 6 (1959); Chem. Abstr., 66, 56501'(1961). (6) iV..\I. Turkevich, I