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
