Synthesis of Potential Antineoplastic Agents. XV. Some 1,4

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Synthesis of PoLeiitial Antineoplastic Agents. h\ Some 1,i-Bisamides of 1,2,3,4-Tetrahydroquinoxaline' '

111 1901 it TI as reported4 that S.S'-~)ii(:i-bi.oniol,ropioiiy1)piperaxiiie (I, X = 131.) produced potent and reproducaible ailtineoplastic :uti\ ity iu niiw. It 11 also shown that the ,&broiiio subst ituciit c~oulclhe rvplaced b y chloro or hy iiietharie~ulfoliylos?~ : ~ n dstill have wtivity iiiaiiitaiiied. Iri vicw of tlic art ivity of I \ r e reportedb thc preparation of ;I seric.:, of :i-cliloropropionyl wmpouiids from :i vnricty of 1iitrogc.n hcterocycslic system>. That 1 ) a p e ~iiitlicantctl that tlic :~-chloropropioiiylslniideiprclxircd wire eswiti:dly i l l active against the Duiiiiiilg leulieniia n i i t l ag:iiii+t Adenocnrcinoriia 755. Xftc>r f he j)uhli(~atioiiof t h t report, however, it T\ as iiotccl that tlic tcltraliydroquinoxalirie derivative I1 exhibited i~eproduc'ihlc :ivtivity6 :tg:iitist the INCOR Tetrahydro base used

R

Quinoline Quinoline Quinoline

CH=CHCH3 CCHI=CHZ CH=CHCeHs

Quinoline

CH=CHCO--N

Isoquinolinec Isoquinoline Isoquinoline Isoquinoline

CHCln CCHa=CHZ CH=CHCHa CH=CHCoH,

Isoqninoline

CH=CHCO-N

9

----

B p (mm) or m p , 'C

Yield, /"

C

158-159 ( 2 ) a 56-5Sb 98-99

73 70 96

77.56 77.56 82.10

196-198

84

87-88 123-124(0.2) 75-76b 109-110d 169-170

Calcd, %--H

%----

S

----Found, C

H

N

7.51 7.51 6.51

6.96 6.96 5.32

77.55 77.30 81.92

7.39 7.45 6.47

6.87 7.00 5.41

76.28

6.40

8.09

76.28

6.40

7.98

78 67 71 99

54.12 77.56 77.56 82.10

4.54 7.51 7.51 6.51

5.74 6.96 6.96 5.32

54.20 77.33 77.51 82.00

4.52 7.47 7.43 6.54

5.84 6.84 6.82 5.36

89

76.28

6.40

8.09

76.07

6.52

8.20