Homologous Series of 3-Alkyl- and 5-Alkyl-5-nitrotetrahydro- -1,3-Oxazines and Their Antitumour Activity
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1 BULLETIN DE L'ACADEMIE POLONAISE DES SCIENCES Serie des sienes himiques Vlume X, N. 7, 1962 ORGANIC CHEMISTRY Hmlgus Series f 3-Alkyl- and 5-Alkyl-5-nitrtetrahydr- -1,3-Oxazines and Their Antitumur Ativity by Z. ECKSTEIN, P. GLUZltfSKI, E. GROCHOWSK1, M. MORDARSKT and T. URBANSKI Presented by T. URBANSKI n May 3, 1962 Our frmer experiments have shwn that the substanes f the general frmula (A), i.e. 5-nitrtetrahydr-l,3-xazine derivatives substituted by alkyls in the psitin 3 and 5 pssess an antitumur ativity bth in vitr [1], [2] and in viv [2]. R 2 /Ox \l I NO->-\ N R 1 (A) T examine the influene f the hain length f the alkyls R 1 and R 2 n the antitumur ativity f mpunds (A), we prepared tw hmlgus series with a varying number f arbn atms in R 1 and R 2 : 1 R 1 = CH 3 and R 2 = frm C 2 t /i-c 5H M ; 2 R' -frm Ci t /;-C u H iy inluding sme isalkyl substituents and R 2 = CH 3 r C 2. Sme f the mpunds btained have nt been s far desribed in the literature. All substanes were prepared by the standard methd frm 2-alkyl-2-nitrprpane-l,3-dils, rrespnding primary amines and frmaldehyde in the mlarati 1:1:1 in aqueus alhl [3] [5] arding t the general equatin: CH 2 OH R2 C N 2 I R'NH 2 + CH 2 I CH 2 OH OH - -> (A) The hydrhlrides f (A) were btained mainly frm the rude bases (A) and then purified by rystallizatin. In sme ases the free base was first islated and purified by fratinal distillatin under redued pressure and then the hydrhlride was preipitated frm aetne r ether slutin using alhli hydrgen hlride. 1331]
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3 Hmlgus Series f 3-Alkyl Table I shws yields and melting pints f hydrhlrides. The physial prperties f the new free bases (A) are given in Table IT. The fllwing general rules an be dedued frm the experimental fats bserved in the urse f preparatin f these mpunds: (1) When 2-nitr-2-methylprpane-l,3-dil was ndensed with amines and frmaldehyde, it was fund that the ability f frming a 1,3-xazine ring dereased with the number f arbn atms in R 1. E.g. the mpund (A), (R 1 = 7J-Ci H 2 1, R 2 = CH 3 ) uld nt be btained, when n-deylamine was used. The preparatin f hydrhlrides f (A) pssessing in the psitin 3 a lng arbn hain (Ri = C 7 C) invlves muh diffiulty beause f their hygrspi prperties. Partiularly the substanes (XXVII) and (XXVIII) (R 1 = «-C 8 H 17 and n-c 9 H 19, respetively) have been analysed and examined as free bases, sine they are deliquesent even when kept under dry ether. (2) The inrease f R 2 in 2-nitr-2-alkylprpane-l,3-dils influenes the ease f frmatin f the 1,3-xazine ring t a muh lesser extent. Only when R 2 was >i-c 17 H 35, the reatin did nt yield an individual substane but a mixture. All attempts t purify it by repeated rystallizatin did nt affrd the xazine. The prdut shwed the presene f an OH band (. 33 m.-') in the lr-spetrum. The mpunds were examined by IR using the Hilger H-8 spetrphtmeter bth as hydrhlrides (in nujl mull) and as free bases (as apillary films f liquids). The spetra f all mpunds (A) have the intense band m. -1 haraterizing asymmetri vibratins f the nitr grup. In all the spetra f hydrhlrides a brad and intensive band (. 25 m.-') is fund harateristi, fr tetrahydr-1,3-xazine hydrhlrides, what nfirms ur frmer bservatins [6]. The IR-spetra f free bases (A) were in agreement with thse expeted n the basis f ur earlier paper [5]. One f the riteria f purity f the substanes was the absene f bands typial fr OH and NH grups. Antitumur ativity All derivatives f 5-nitrtetrahydr-l,3-xazine desribed in the present paper were examined frm the pint f view f their antitumur ativity in vitr. Ehrlih asites arinma and Amytal asites sarma were examined using the same methd as previusly desribed [7]. The results btained in the present wrk are lleted in Table III, tgether with the data btained in the frmer experiments [1], [2]. Fr mparisn f their antitumur ativity a number f 5-nitrtetrahydr-l,3-xazine derivatives previusly prepared and desribed [5] are als inluded in Table III. Amng 1,3-xazines f the first series (I XII) with varying number f arbn atms in R 2 (A) (R 2 frm CH 3 t /i-ci 5 H 3 r, R 1 = CH 3 ) the mst effetive were the derivatives f nitrethane (1); (A) (R 2 - CH 3 ) and l-nitr-«-hxane (V); (A) (R 2 = H-C 5 H n ). Less effetive were derivatives f l-nitr-/t-tane (VII); (A) (R 2 = n-c 7 Hi 5 ), l-nitr-/t-deane (IX); (A) (R 2 = /i-c 9 Hig) and 1-nitr-n-
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6 336 Z. E k s t e i n et al. -heptane (VI); (A) (R 2 -- ;;-C Hi,). The lwest ativity was exhibited by the derivative f l-nitr-/;-pentane (TV); (A) (R 2 = /7-C 4 H G ), whih is almst inative. All the thers were apprximately f equal effiieny. Amng the prduts f the send series (XIII XXVIII) ntaining varius arbn hains in R 1, (A) (R 1 frm C 2 t W-C9H19; R 2 CH., r C 2 ) the derivative f «-tylamine (XXVII) (A). (R 1 = n-c 8 H 1 7 ; R 2 = CH3), exhibited the highest ativity against bth kinds f ells. A relatively high ativity was bserved f the xazins deriving frm nitrethane and is-prpyl- and is-butylamine (XVI) and (XX) (A) (R 1 /-C,H 7 ; R 2 CH,) and (A) (R> i-c 4 H 9 ; R 2 = CH,), respetively. It is f interest that the derivative f 1-nitrprpane and n-hexylamine (XXIV) (A) (R 1 n-c^hn', R 2 = C 2 ) shwed a speifi high ativity against Amytal asites sarma. It exerted a very lw ativity against Ehrlih asites arinma. The derivative f //-prpylamine and nitrethane (XIV) (A) (R 1 /;-C,H 7 ; R2 = CH,) shwed the lwest ativity. It was mpletely inative against Ehrlih asites arinma and f lw ativity against ther ells examined. A lw ativity was als demnstrated by the mpunds (XIX) and (XXV11I) (A)(Ri =«-C 4 H 9 ; R 2 C 2 and R 1 /J-C 9 H, 9 ; R 2 CH.;, respetively). All ther mpunds f this sries exhibited an apprximately equal relatively lw ativity. N general rule as t the antitumur ativity as funtin f the struture f 5-nitrtetrahydr-l,3-xazine derivatives an be drawn s far. The present paper nstitutes the publiatin LI I frm the series n "Reatins f Aliphati Nitrmpunds". INSTITUTE OF ORGANIC SYNTHESIS, POLISH ACADEMY Ol SCIENCES (ZAKLAD SYNTEZY ORGANICZNEJ, PAN) OF INSTITUTE OF IMMUNOLOGY AND EXPERIMENTAL THERAPY, WROCLAW. POLISH SCIENCES (INSTYTUT IMMUNOLOGII I IIRAPII DSWIADC'ZALNEJ, WROCLAW, PAN) ACADEMY REFERENCES l] S. Slpek, H. Mrdarska, M. Mrdarski, T. Urbahski, D. Giirne, Bull. Aad. Pln. Si, Ser. si. him., gel. t gegr., 6 (1958), 361. [21 T. Urbahski, D. Giirne, S. Slpek. H. Mrdarska, M. Mrdarski, Nature, 187 (I96), 426. [3] M. Senkus, J. Am. Chem. S.. 72 (195), [4] T. Urbahski, H. D;)brwska, B. Lesiwska, H. Pitrwska, Rzniki Chem., 31 (1957) [5] Z. Ekstein, P. G111/1 riski, W. Hfman, T. Urbanski,.1. Chem.. S, (1961), 489. [6] Z. Ekstein, A. Saha, T. Urbahski, Tetrahedrn. 16 (1961), 3. [7] S, Slpek, H M rdarska, T. Urbahski, B.Skwrhska-Serafin. H.lJahrwska. Bull. Aad. Pln. Si., Ser. si. him.. gel. et gegr., 6 (1958), 355.
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