Synthesis, characterization and biological activity of (Z)-1-[2]-1-cyclopentanol and their arylhalostannyl derivatives

Article abstract of DOI:10.1016/S0277-5387(98)00027-8

The synthesis and characterization by elemental analysis, IR and ¹H NMR of (Z)-1 - 1-cyclopentanol,CH₂(CH₂)₃C(OH)CHCHSnPh ₃ (1) and (Z)-1 - 1-cyclopentanol, CH₂(CH₂)₃C(OH)CHCHSn(p-toly)₃ (2) are described, together with their halodemetallation by I₂, Br₂ and ICl to yield derivatives of the types CH₂(CH₂)₃C(OH)CHCHSnAr_3-nX _n (Ar = phenyl or p-tolyl ; n = 1, 2 ; X = I, Br, Cl). The solid-state structures of two compounds have been determined by X-ray diffraction analysis. In the crystal of CH₂(CH₂)₃C(OH)CHCHSnph₃ (1) the Sn atom has a distorted tetrahedral geometry but intramolecular contact with the hydroxyl O atom has not been found. A trigonal bipyramidal geometry is found in CH₂(CH₂)₃CC(OH)CHCH SnphBr₂(11), in which OSn - interaction is noted [2.446(8) A] The biological activity of the title complexes is also investigated.

Full text of DOI:10.1016/S0277-5387(98)00027-8

Polyhedron Vol[ 06\ No[ 04\ pp[ 1492Ð1498\ 0887
Þ 0887 Elsevier Science Ltd
Pergamon
All rights reserved[ Printed in Great Britain
9166Ð4276:87 ,08[99¦9[99
\
PII ] S9166Ð4276"87#99916Ð7
Synthesis\ characterization and biological
activity of "Z#!0!ð1!"triarylstannyl#vinyŁ!0!
cyclopentanol and their arylhalostannyl
derivatives
Hui Cong Dai\aꢀ Qi Hua Ying\a Xiao Hong Wang\a Su Mei Yue\a
Hua De Pan\a Xi Chen\b
a Department of Chemistry\ Northeast Normal Univeristry\ Changchun 029913 P[R[ China
b Department of Medical laboratory\ Jilin Medical College\ Jilin\ 029910 P[R[ China
"Received 4 September 0886 ^ accepted 6 January 0887#
0
Abstract*The synthesis and characterization by elemental analysis\ IR and H NMR of "Z#!0!ð1!"triphenyl!
stannyl#vinylŁ!0!cyclopentanol\CH1"CH1#2C"OH#CH1CHSnPh2 "0# and "Z#!0!ð1!"tri!p!toyl!stannyl# vinylŁ!0!
cyclopentanol\ CH1"CH1#2C"OH#CH1CHSn"p!toly#2 "1# are described\ together with their halodemetallation
by I1\ Br1 and ICl to yield derivatives of the types CH1"CH1#2C"OH#CH1CHSnAr2!nXn "Ar ꢁ phenyl or
p!tolyl ^ n ꢁ 0\ 1 ^ X ꢁ I\ Br\ Cl#[ The solid!state structures of two compounds have been determined by X!ray
di}raction analysis[ In the crystal of CH1"CH1#2C"OH#CH1CHSnph2 "0# the Sn atom has a distorted tetra!
hedral geometry but intramolecular contact with the hydroxyl O atom has not been found[ A trigonal
bipyramidal geometry is found in CH1"CH1#2CC"OH#CH1CH SnphBr1"00#\ in which OSn0 interaction is
noted ð1[335"7# AýŁ The biological activity of the title complexes is also investigated[ Þ 0887 Elsevier Science
Ltd[ All rights reserved
Keywords] synthesis structure ^ cyclopentanol ^ biological activity
———————————————————————————————————————————————
Iododemetallation ð0Ł of the products of the reactions tural features\ particularly the coordinative HO0Sn
between triphenyltin hydride and ethynyl"hydroxy# interactions are compared[
steroids ð1\2Ł yield diorganotin diiodides with inter!
esting antitumour activities ð3\4Ł[ Because each of
these species exhibits an intramolecular HO0Sn
interaction giving rise to a _ve!membered tin!con!
EXPERIMENTAL
taining ring\ we described here another class of related
compounds\ namely "Z#!0!ð 1!"triarylstannyl# vinylŁ!
Rea`ents and apparatus
0!cyclopentanols as well as some of the corresponding
0!Ethynylcyclopentanol\ triphenyltin hydride and
tri!tolyltin hydride were prepared by literature
method ð5\6\7Ł[
All reagents were of analytical or guaranteed qual!
ity[
IR spectra were recorded on an Alpha Centalrt
spectrometer "3999Ð399 cm−0 range# as KBr pellets[
0H NMR spectra were recorded in CDCl2 on a JEOL
JNM!FX 099 instrument[
diarylhalostannyl!
and
aryldihalostannyl!com!
pounds[ Our strategy was to develop novel organotin
compounds containing a cyclopentanoid ligand with!
out the steroid moiety[ A second goal in our strategy
is to indentify structural elements in the organotin
steroids and cyclopentanoids\ which are essential for
the antitumor activity[ In the mean time\ their struc!
Crystal data were collected at 19>C on a Siemens P3
di}ractometer with graphite!monochromated MoÐKa
ꢀ Author to whom correspondence should be addressed[
1492

1493
H[ C[ Dai et al[
radiation "l ꢁ 9[60962 _#[ The structure was solved evaporated o} and the residue was recrystallized three
using SHELXTL!PLUS"Siemens# direct methods[
times from cyclohexane to yield 9[6 g of compound 4[
The other vinylphenyltin halides were prepared
analogously by the use of ICl "chlorides# or I1
"iodides#[
Analytical procedures
Abbreviations[ 0H NMR data ] s ꢁ singlet ^ d ꢁ
doublet ^ m ꢁ complex pattern ^ b ꢁ broad[ All coup!
ling constants are in hertz[
Elemental analyses were carried out with a PerkinÐ
Elmer PE 1399 C\H\ N instrument[
"Z#!0!ð1!"triphenylstannyl#vinylŁ!0!cyclopentanol\
0[ Yield ] 57) ^ m[p[ "recrystallized from ethanol# ]
68Ð79>C[ Elemental analysis ] Found"Calc[# ] C\ 54[0
"53[8# ^ H\ 4[5 "4[5# ^ Sn\ 14[7 "15[9#)[ IR ] n"O0H# ]
2467 ^ n"C0O#\ 0962 cm−0[ 0H NMR ] 0[922 "s\OH# ^
0[2Ð0[7 "m\C4H7# ^ 5[102 "d"01[3#\ CH0Sn# ^ 6[931
"d"01[3#\ CH#\ 6[1Ð6[4 "m\ meta¦para#[
Synthesis
Compound 0[ 0!Ethynylcyclopentanol "8[2 g\ 73[ 4
mmol# and dibenzoyl peroxide "299 mg# were added
to an ether solution of triphenyltin hydride prepared
from 2[4 g "89[8 mmol# of LiAlH3 and 24 g "89[8
mmol# triphenyltin chloride[ The mixture was stirred
for 29 h at room temperature under nitrogen[ The
ether was evaporated o} and the residue was recrys!
tallized three times from ethanol to yield 15 g of com!
pound 0 and 6[6 g of hexaphenylditin\ m[p[ 122Ð123>C
ð0Ł as a by!product[
Compound 1[ The same procedure was used for the
raction of 0!ethynylcyclopentanol with tri!p!tolyltin
hydride[
Compound 4[ A solution of bromine "9[205 g\ 0[87
mmol# in 09 ml of CCl3 was added dropwise with
stirring to an ice!cooled solution of 9[ 802 "0[87 mmol#
"Z#!0!ð1!"tri!p!tolylstannyl#vinylŁ!0!cyclopentanol\
1[ Yield ] 52) ^ m[p[ "recrystallized from ethanol# ]
018Ð029>C[ Elemental analysis ] Found "Calc[# ]
C\56[00"55[71# ^ H\ 5[39 "5[30# ^ Sn\ 12[59 "12[47#)[
0
IR ] n"O0H#\ 2464 ^ n"C!O#\ 0957 cm−0[ H NMR ]
9[88 "s\OH# ^ 0[4Ð0[7 "m\ C4H7# ^ 1[21 "s\ CH2# ^ 5[ 09
"d"01[3#\ CH!Sn#\ 5[81 "d"01[3#\ CH# ^ 6[134 "d\ "6[7#\
meta# ^ 6[593 "d"6[7#\ ortho#[
"Z#!0!ð1!"chlorodiphenlstannyl#vinylŁ!0!cyclopen!
tanol\ 2[ Prepared from 0 and ICl in a 0 ] 0 molar
ratio at −09>C Yield ] 65) ^ m[p[ "recrystallized from
cyclohexane# ] 038Ð049>C[ Elemental analysis ]
of 0 in 01 ml of CCl3[ The colour disappeared immedi! Found"Calc[# ] C\ 42[84 "43[28# ^ H\ 4[97 "4[94# ^ Sn
ately[ The mixture was allowed to warm to room 17[7 "17[2#)[ IR ] n"O0H#\ 2313 ^ n"C0O#\ 0965
temperature and set aside for 4 h[ The solvent was cm−0 0H NMR ] 1[21 "s\OH# ^ 0[3Ð0[7 "m\ C4H7# ^
[
Table 0[ Crystallographic data for compounds 0[ and 00[
Formula
Formula weight
Space group
a "_#
C14H15OSn
350[04
P10:c
C02H05Br1OSn
355[65
P101010
7[564"3#
7[216"1#
b "_#
c "_#
05[678"2#
04[406"2#
81[20"2#
1056[4"7#\3
0[302
01[412"6#
03[998"7#
89"1#
0410[8"1#\3
0[803
b">#
V"_2#
Dcalc"mg m2#
Y"mm−0
F"999#
#
0[089
825
0[990
873
Radiation "_#
9[60962
9[60962
Scan range ">#
0[68 ³ u ³ 14[90
9[31×9[39×9[25
4018
1[05 ³ u ³ 01[22
9[21×9[17×9[39
0245
Crystal size "mm#
Re~ections collected
Re_nement method
Data:restrain:para
Goodness!of!_t on F1
R0\ðI × 15"I#Ł
Full!matrix Least!squares on F1
2791:9:292
0[952
Full!matrix Least!square on F1
0245:9:87
0[028
9[9348
9[930
WR1\ðI × 15"I#Ł
9[0087
9[921
Largest di}[ Peak and hole "e _−2
Index range
#
9[643Ð0[491
−0 ³ h ³ 8
−0 ³ k ³ 08
−07 ³ l ³ 07
9[5236Ð0[945
9 ³ h ³ 00
9 ³ k ³ 04
9 ³ l ³ 06

Analysis of "Z#!0!ð1!"triarylstannyl#vinylŁ!0!cyclopentanol
1494
5[133 "d"00[2#\ CH0Sn# ^ 5[891 "d"00[2#\ CH# ^ 6[1Ð
"Z#!0!ð1!"dichloro!p!tolylstannyl#vinylŁ!0!cyclo!
6[4 "m\meta¦para# ^ 6[5Ð6[7 "m\ ortho#[
pentanol\ 09[ Prepared from 1 and ICl in a 0 ] 1 kmolar
"Z#!0!ð1!"chlordi!p!tolylstannyl#vinylŁ!0!cyclopen! ratio at −09>C\ then allowed to warm to room tem!
tanol\ 3[ Prepared from 1 and ICl in a 0 ] 0 molar perature[ Yield ] 35)[ m[p[ "recystallized from
ratio at −09>C[ Yield ] 46)[ m[p[ "recrystallized from CHCl2:petroleum ether "0 ] 0# ] 098Ð009>C[ Elemental
cyclohexane:CCl3 "0 ] 0# ] 034Ð035>C[ Elemental analysis ] Found"Calc[# ] C\ 31[92 "31[80# ^ H\ 3[48
analysis ] Found"Calc[# ] C\ 45[20 "45[24# ^ H\ 4[47 "3[52# ^ Sn\ 18[83 "29[18#)[ IR ] n"O0H#\ 2432 ^
0
"4[52# ^ Sn\ 15[40 "15[41#)[ IR ] n"O0H#\ 2423 ^ n"C0O#\ 0954 cm−0[ H NMR ] 2[9 "s\ OH# ^ 0[3Ð0[7
n"C0O#\ 0955 cm−0[ 0H NMR ] 1[06 "s\ OH# ^ 1[24 "s\ "m\ C4H7# ^ 1[26 "s\ CH2# ^ 5[123 "d"09[3#\ CH0Sn# ^
CH2# ^ 0[65 "b\C4H7# ^ 5[123 "d 00[2#\ CH!Sn# ^ 5[847 "d"09[3#\ CH# ^ 6[147 "d"7#\ meta# ^ 6[554 "d\
5[728"d"00[2#\ CH# ^ 6[100 "d"7#\ meta# ^ 6[517 "d"7#\ ortho#[
ortho#[
"Z#!0!ð1!"dibromophenylstannylŁ!0!cyclopentanol\
"Z#!0!ð1!"bromodiphenylstannyl#vinylŁ!0!cyclo! 00[ Prepared from 0 and Br1 in a 0 ] 1 molar ratio at
pentanol\ 4[ Prepared from 0 and Br1 in a 0 ] 0 ratio at −09>C\ then allowed to warm to room temperature[
−09>C[ Yield ] 65)[ m[p[ "recrystallized from Yield\ 43[2)[ m[p[ "recrystallized from cyclohexane:
cyclohexane# ] 032Ð033>C[ Elemental analysis ] CCl3# ] 091!092>C Elemental analysis ] Found"Calc[# ]
Found"Calc[# ] C\ 38[04 "38[07# ^ H\ 3[59 "3[45# ^ Sn\ C\ 22[37 "22[34# ^ H\ 2[40 "2[35# ^ Sn\ 14[27 "14[32#)[
0
14[38 "14[47#)[ IR ] n"O0H#\ 2381 ^ n"C0O#\ 0963 IR ] n"OÐH#\ 2389 ^ n"C0O#\ 0961 cm−0[ HNMR ]
cm−0 0H NMR ] 1[16 "s\ OH# ^ 0[3Ð0[7 "b\ C4H7# ^ 1[86 "s\ OH# ^ 0[3Ð0[7 "m\ C4H7# ^ 5[293 "d"09[3#\
[
5[184 "d"00[2#\ CH0Sn# ^ 5[760 "d"00[1#\ CH ^ 6[1Ð6[4 CH0Sn# ^ 5[762 "d"09[3#\ CH ^ 6[2Ð6[4 "m\ met!
"m\ meta¦para# ^ 6[5Ð6[7 "m\ ortho#[
a¦para# ^ 6[6Ð6[7 "m\ ortho#[
"Z#!0!ð1!"bromo!di!p!tolylstannyl#vinylŁ!0!cyclo!
"Z#!0!0ð1!"dibromo!p!tolylstannyl#vinylŁ!0!cyclo!
pentanol\ 5[ Prepared from 1 and Br1 in a 0 ] 0 molar pentanol\ 01[ Prepared from 1 and Br1 in a 0 ] 1 molar
ratio at room temperature[ Yield\ 37[9)[ m[p[ "recrys! ratio at −09>C\ then allowed to warm to room tem!
tallized from cyclohexane# ] 033Ð034>C[ Elemental perature[ Yield ] 31)[ m[p[ "recrystallized from
analysis ] Found"Calc[# ] C\ 40[13 "40[15# ^ H\ 3[83 cyclohexane:CCl3"0 ] 0## ] 87Ð88>C[ Elemental analy!
"4[01# ^ Sn\ 12[88 "13[02#)[ IR ] n"OH#\ 2425 ^ sis ] Found"Calc[# ] C\ 24[91 "23[86# ^ H\2[62 "2[66# ^
n"C0O#\ 0961 cm−0[ 0H NMR ] 1[09 "s\ O0H# ^ 0[3Ð Sn\ 13[60 "13[58#)[ IR ] n"O0H#\ 2366 ^ n"C0O#\
0[7 "b\ C4H7# ^ 1[24 "s\ CH2# ^ 5[185 "d"00[2#\ CH0Sn# ^ 0956 cm−0
5[755 "d"00[2#\ CH# ^ 6[105 "d"7#\ meta# ^ 6[523 "d"7#\ C4H7# ^ 1[26 "s\CH2# ^ 5[299 "d "09[0##\ CHÐSn# ^ 5[765
orthoŁ[ "dd"09[1\2[9#\CH# ^ 6[143 "d"7#\meta# ^ 6[541
"Z#!0!ð1!"iododiphenylstannyl#vinylŁ!0!cyclopen! "d"7#\ortho#[
tanol\ 6[ Prepared from 0 and I1 in a 0 ] 0 molar ratio at "Z#!0!ð1!"didiodophenylstannyl#vinylŁ!0!cyclo!
[
0H NMR ] 1[66 "s\ OH# ^ 0[2Ð0[7 "m\
room temperature[ Yield\ 59[6)[ m[p[ "recrystallized pentanol\ 02[ Prepared from 0 and I1 in a 0 ] 1 molar
from cyclohexane# ] 015Ð016>C Elemental analysis ] ratio at room temperature[ Yield\ 59[5)[ m[p[ "recrys!
Found"Calc[# ] C\ 33[57 "33[54# ^ H\ 3[08 "3[03# ^ Sn\ tallized from cyclohexane# ] 007Ð019>C Elemental
11[18 "11[12#)[ IR ] n"O0H#\ 2309 ^ n"C0O#\ 0961 analysis ] Found"Calc[# ] C\ 16[74 "16[72# ^ H\ 1[89
cm−0 0H NMR ] 1[60 "s\ OH# ^ 0[3Ð0[7 "b\ C4H7# ^ "1[77# ^ Sn\ 10[10 "11[05#)[ IR ] n"O0H#\ 2368 ^
[
5[266 "d"00[1#\ CH0Sn# ^ 5[688 "d"00[1#\ CH# ^ 6[1Ð n"C0O#\ 0955 cm−0[ 0HNMR ] 1[40 "s\ OH# ^ 0[3Ð0[7
6[4 "m\ meta¦para# ^ 6[5Ð6[7 "m\ ortho#[ "m\ C4H7# ^ 5[399 "d"09[2#\ CH0Sn# ^ 5[516
"Z#!0!ð1!"iododi!p!tolylstannyl#vinyl#!0!cyclopen! "d"09[2#\CH# ^ 6[1Ð6[5 "m\meta¦para# ^ 6[6Ð6[7 "m\
tanol\ 7[ Prepared from 1 and I1 in a 0 ] 0 molar at ortho#[
room temperature[ Yield\ 50)[ m[p[ "recrystallized
"Z#!0!ð1!"diiodo!p!tolylstannyl#vinylŁ!0!cyclo!
from cyclohexene# ] 85Ð86 _[ Elemental analysis ] pentanol\ 03[ Prepared from 1 and I1 in a 0 ] 1 molar
Found "Calc[# ] C\ 35[64 "35[67# ^ H\ 3[60 "3[56# ^ Sn\ ratio at room temperature[ Yield ] 41)[ m[p[ "recrys!
11[09 "11[91#)[ IR ] n"O0H#\ 2447 ^ n"C0O#\ 0948 tallized from cyclohexane:CCl3 "0 ] 0## ] 090Ð091>C[
cm−0[ 0H NMR ] 0[80 "s\ OH# ^ 0[3Ð0[7 "b\ C4H7# ^ 1[23 Elemental analysis ] Found"Calc[# ] C\ 17[85 "18[13# ^
"s\ CH2# ^ 5[ 271 "d"00[3#\ CH0Sn# ^ 5[681 "d"00[2#\ H\ 2[10 "2[05# ^ Sn\ 19[47 "19[53#)[ IR ] n"O0H#\
0
CH# ^ 6[103 "d"7#\meta# ^ 6[524 "d"7#\ ortho#[
2423 ^ n"C0O#\ 0948 cm−0[ H NMR ]1[32 "s\ OH# ^
"Z#!0!ð1!"dichlorophenylstannyl#vinylŁ!0!cyclo! 0[3Ð0[7 "m\ C4H7# ^ 1[17 "s\ CH2# ^ 5[49 "d"09[93#\
pentanol\ 8[ Prepared from 0 and ICl in a 0 ] 1 molar CH0Sn# ^ 6[92 "d "09[93#\ CH# ^ 6[ 02Ð6[52 "m\ meta¦
ratio at −09>C then allowed to warm to room tem! para# ^ 6[58Ð6[70 "m\ ortho#[
perature[ Yield ] 41)[ m[p[ "recrystallized from
CHCl2:petroleum ether "0 ] 0\ 29:59>C# ] 010Ð011>C[
Elemental analysis ] Found"Calc[# ] C\ 30[16 "30[21# ^
RESULTS AND DISCUSSION
H\ 3[15 "3[16# ^ Sn\ 20[39 "20[30#)[ IR ] n"O0H#\
0
2333 ^ n"C0O#\ 0956 cm−0[ H NMR ] 2[17 "s\ OH# ^ Synthesis
0[3Ð0[7 "m\ C4H7# ^ 5[088 "d"09[3#\ CH0Sn# ^ 5[845
"d"09[3#\ CH# ^ 6[2Ð6[4 "m\ meta¦para# ^ 6[6Ð6[8 "m\
ortho#[
The
"Z#!0!ð1!"triarylstannyl#vinylŁ!0!cyclopen!
tanols "aryl ꢁ phenyl\ p!tolyl# were synthesized by the

1495
H[ C[ Dai et al[
addition of the corresponding triaryltin hydride to the shift to down_eld compared with 0 and 1[ The nJCHꢁCH
triple bond of 0!ethynyclcyclopentanol[
coupling consistants decrease in the following order
SnAr2 ³ SnAr1X ³ SnArX1[
Solid!state structures
The molecular structure of 0 and 00 are shown in
Figs 0Ð1\ respectively and selected interatomic bond
distances "_# and angles "># are listed in Table 1[ The
Sn atom in 0 is bound to three phenyl groups as well
as to the C"6# atom of the vinyl residue ðSn0C"6#\
1[023 _Ł leading to a distorted tetrahedral geometry[
The tetrahedral angles range from 099[7> to 019[5>[
There is a Z con_guration at the double bond[ It is
possible that there is weak interaction between Sn
atom and O atom\ for the presence of O atom in~u!
ences the strength of Sn0C"ph# bonds[ From Table
1 we can see the bond distance of Sn0C"03# is longer
than that of Sn0C"7# and Sn0C"19#\ respectively[
From above\ we can see the di}erences between 0 and
steroidal compounds[ In steriods\ there is an intra!
molecular coordination from O to Sn ð0Ł\ and\ the
central tin atom has a strongly distorted trigonal
bipyramidal geometry[
Scheme 0
Scheme 1
The structure of 00 is shown in Fig[ 1[ The tin atom
is _ve coordinated[ The geometry about the tin atom
is based on a trigonal bipyramid with the trigonal
plane de_ned by the Br"1#\ C"0# and C"6#atoms\ while
the Br"0# and O atom is in the axial position
"Br"0#0Sn0O ꢁ 058[8 _#[ The Sn0Br bond dis!
tances are not equal\ for the bond distance of
Sn0Br"0# "1[471 _# is signi_cantly longer than that
of Sn0Br"1# "1[389 _#[ This di}erence may be ration!
alized in terms of the former bond being apical and
the latter equatorial[ The _ve!membered chelate ring
is almost planar[
Scheme 2
The reactions of 0 and 1 with halogens in a 0 ] 0 or
0 ] 1 molar ratio yield the corresponding mono! or di!
halides\ respectively[
IR and 0H NMR data
0
The IR and H NMR data are consistent with the
expected structures[ They are given in the exper!
imental details[
Biolo`ical activity
IR data shows that all the compounds exhibit the two
characteristic O0H and C0O stretching vibrational
The data summarized in Tables 2 and 3 show that
peaks[ In the 0H NMR\ "0CH1CH0# of all halides dihalides and aductor display inhibitory action to
Table 1[ Selected bond lengths "_# and angle ">#
0
00
Bond
Bond
dist[
Bond
Angle
Bond
dist[
Angle
Sn0C6
Sn0C7
Sn0C19
Sn0C03
C50C6
O0C4
1[023"8#
1[024"6#
1[037"5#
1[052"5#
0[186"01#
0[327"8#
0[357"09#
C60Sn0C19
C190Sn0C7
C190Sn0C03
C60Sn0C7
C60Sn0C03
C70Sn0C03
Br"1#0Sn0C"0#
C"0#0Sn0C"6#
002[0"2#
097[2"1#
095[8"1#
019[5"2#
099[7"2#
094[8"1#
096[6"2#
022[0"4#
Sn0Br"1#
Sn0C"6#
Sn0Br"0a#
Sn0C"0#
Sn0O
1[389"1#
1[984"03#
1[471"1#
1[048"00#
1[335"7#
1[471"1#
0[334"03#
C"0#0Sn0O
76[3"3#
87[9"0#
85[0"3#
001[5"3#
76[9"1#
60[7"3#
88[9"2#
058[8"1#
Br"1#0Sn0Br"0a#
C"6#0SnBr"0a#
Br"1#0Sn0C"6#
B"1#0Sn0O
C"6#0Sn0O
C"0#0Sn0Br"0a#
O0Sn0Br"0a#
Br"0#0Sna
C"8#0O
C40C5

Analysis of "Z#!0!ð1!"triarylstannyl#vinylŁ!0!cyclopentanol
1496
Fig[ 0[
Fig[ 1[

1497
H[ C[ Dai et al[
Table 2[ Inhibitory e}ect of the compounds on some tumor cells "MTT#
a
Comound
Tumor cell
KB
Dose "mM# Inhibitory rate")#
IC49
9[53
9[66
9[69
9[29
9[39
9[95
9[91
9[69
9[69
9[69
9[59
9[69
Estimationb
0
9[0
0
4
9[0
0
2[9
62[9
77[6
1[7
¦¦
Bel
63[6
63[6
15[5
28[5
88[8
23[9
65[9
73[1
17[8
50[1
88[1
56[9
61[6
88[4
25[4
70[6
85[2
09[4
50[6
¦¦
4
9[0
0
09
9[0
0
09
9[0
0
09
9[0
0
09
9[0
0
09
9[0
0
4
HCT
B05
¦¦
¦¦
8
B05
¦¦
00
Bel
¦¦¦
¦¦¦
¦¦
B05
02
HCT
Bel
09
099
9[0
0
09
9[0
0
09
9[0
0
09
9[0
0
09
9
24[6
88[4
43[0
47[0
82[4
20[7
33[0
87[4
00[2
51[3
88[6
¦¦
B05
¦¦
Beap
Escl
¦¦
¦¦
a Drug concentration required to inhibit tumor cell by 49)[
b ¦¦ ] "9[0 ¾ IC49 ³ 0#\¦¦¦ ] "IC49 ³ 9[0#

Analysis of "Z#!0!ð1!"triarylstannyl#vinylŁ!0!cyclopentanol
1498
Table 3[ Immunocompetence assay of the compounds on
celiac mastocyte of rat
in antitumor but also in immunity\ possibly serves as a
suitable model for achieving a tin!ligand con_guration
optimal with regards to its antitumor activity or
immunity activity[ The results obtained merit further
studies on the structure!activity relationship of anti!
tumor or immunity organotin compounds of this type[
Dose
"mM#
Inhibitory
rate")#
Compound
Estimationa
0
3
19
199
19
199
19
199
19
199
19
56[7
87[8
58[1
75[1
86[4
86[4
50[1
86[4
86[4
86[4
86[6
86[6
¦¦
REFERENCES
¦¦
5
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8
00
02
199
19
199
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a ¦¦ ] ðInhibitory rate − 49) "Dose ꢁ 19#Ł\ ¦¦¦ ]
ðInhibitory rate − 89) "Dose ꢁ 19#Ł
tumor cells "B05\ HCT\ Bel\ Beap and Escl# and immu!
competence assay on celiae mastocyte of rat[
The idea of including cyclopentanoidal structure
into antitumor organotin compounds has proven to
be fruitful[ The compounds used to test proved to be
active[ Compound 00\ being the most active not only
7[ Lorenz\ D[ H[\ Shapiro\ P[\ Stern\ A[ and Becker\
E[ I[\ J[ Or`[ Chem[\ 0853\ 17\ 1224[