JABBAR et al., Orient. J. Chem., Vol. 34(4), 2026-2030 (2018)
2027
Carbamate-bearing molecules linked to compound 2
through amide bond. carbamate-bearing molecules
play an important role in modern drug discovery
and medicinal chemistry. Organic carbamates
added with stirring. The stirring was continues for
1 h at room temperature . the precipitate collected
and recrystallized from methanol and the required
compound was obtained as orang solid .M.WT=244,
M.F=C H N O , m.p=142-144 , R :0.56 (ethanol
(
or urethanes) are structural elements of many
14
16
2
2
f
approved therapeutic agents. Structurally, the
carbamate functionality is related to amide-ester
hybrid features and, in general, displays very good
chemical and proteolytic stabilities. This is mainly
due to their chemical stability and capability to
permeate cell membranes. Another unique feature
of carbamates is their ability to modulate inter-
and intramolecular interactions with the target
enzymes or receptors.Therefore a carbamate offers
opportunities for modulation of biological properties
and improvement in stability and pharmacokinetic
:
chloroform, UV active). The elemental Analysis:
found C, 68.91 Cal. C, 68.83 ; found H, 6.60, Cal.
-
1 6
H, 6.60; found N, 11.48, Cal. N, 11.47 , IR (cm ) :
2
1
941(C-H str. CH Asy.) , 2852 C-H str. CH sy.),
2 2
348 (C-N aliphatic), 1469-1412 (C=C Ar.), 3043
(
C-H str. Ar.), 1732 (C=O indole), 1612(CO-NH) ,
860-762 (HC= Ar. bending).
Synthesis of (Z)-3-hydrazono-1-(piperidin-1-
ylmethyl)indolin-2-one(compound2) .
7
5
properties .
The compound 2 has been synthesized
as follows, as shown in scheme 1: compound-1
MATERIALS AND METHODS
(
(
0.005mole, 0.7gr)was dissolved in methanol
10mL) and added hydrazine hydrate (80% ) while
Chemicals and Reagents
shaking. the reaction mixture was refluxed for
0 min. then the solution was allowed to cool to RT
All solvents used were of laboratory grade ,
Ethyl chloroformate (ECF) was obtained from Sigma
Aldrich/Germany, Boc-L glycine;Boc-L-alanine, Boc-L-
valineandBoc-L-prolinewereobtainedfromShanghai
WorldYangChemical/China.IsatinandPiperidinewere
obtained from Sigma Aldrich/Germany.
3
and left at refg. overnight and the product obtained
was recrystallized from petroleum ether as yellow
ppt., m.p=165-170, M.WT=258, M.F=C H N O,
14 18
4
R :0.54 (ethanol :chloroform , UV active). The
f
elemental Analysis: found C, 65.17, Cal. C,65.09 ;
found H, 7.03, Cal. H, 7.02 ; found N, 21.71, Cal. N,
Apparatus
-
1 7
Melting points (uncorrected) were
determined using electrical melting point apparatus,
Electro-thermal 9300, USA. The IR spectra were
recorded in KBr disk on FT-IR spectrophotometer
21.69 , IR (cm ) : 1660 (C=N); 1550-1464 (C=C
Aromatic); 3357, 3155 (N-H str. ), 3064 (C-H Ar.);
1685 (C=O amide isatin), 931-677(HC= Ar.bending),
2931-2850(C-H aliphatic).
/
Shimadzu. Compounds were routinely checked
for their purity on Silica gel G (Merck) Thin layer
chromatography (TLC) plates. Iodine chamber and
UV lamp were used for visualization of TLC spots.
Elemental data for C, H, and N were performed by
Euro-vector EA 3000A, Italy.All the compound have
presented satisfactory chemical analysis.
General procedure for synthesis of compounds (3a-d)
Compound(3a-d)havebeen synthesizedby
8
the mixed anhydride method , as shown in (scheme 1).
ToasolutionofBoc-aminoacid(2.28mmol,0.4gr)was
dissolved in Tetrahydrofuran, THF (5mL) containing
0
TEA (2.28 mmol, 0.24gr) at -10 C were added Ethyl
chloroformate,ECF(2.28mmol,0.24gr)dropwiseover
a period of 10 min. and the mixture was continuously
stirred for further 30 min. the solid was filtered off and
filtrate was added to the solution of compound 2( 2.28
mmol, 0.58gr) containing TEA (2.28 mmol, 0.24gr) in
Synthesis of 1-(piperidin-1-ylmethyl)indoline-2,3-
dione (compound-1) .
The compound 1 has been synthesized
as follows, as shown in scheme 1: Isatin(2,3-
indolineendione) (1gr,0.00679 mole) was dissolved
in (10mL) methanol and then formaladehyde
6
5
mL DMF for 10 min. and the mixture was stirred for
3
7%, 2mL was added to the mixture. The reaction
30 min. at room temperature. The solvent DMF was
evaporated andThe precipitate was collected and was
washed with ether.
0
mixture was cooled to 0 C and then piperidine
(
hexahydropyridine) (00679 mole, 0.57gr) was