In vitro anti-leishmanial activities of germatranyl and Silicon incorporated diorganotin derivatives: Synthesis and spectroscopic properties

Figures & data

Scheme 1.  Synthesis of Diorganotin derivatives.

Table I.  Physico-analytical data for compounds^*of general formula.

				Elemental Analysis Calculated (Found) %
S. No.	R^1	R^2	Molecular formula (Mol. Wt.)	C	H	N	M.P. (^oC)	Yield (%)
1	C6H5	H2CSi(CH3)2C6H5	C48H66O10N2Si2Ge2Sn (1150)	50.07 (50.03)	5.70 (5.56)	2.43 (2.48)	192–194	79
2	p-CH3C6H4	H2CSi(CH3)2C6H5	C50H70O10N2Si2Ge2Sn (1180)	58.52 (58.40)	5.02 (5.10)	2.00 (2.40)	175–177	60
3	p-FC6H4	H2CSi(CH3)2C6H5	C48H64O10F2N2Si2Ge2Sn (1186)	48.53 (48.50)	5.39 (5.35)	2.36 (2.40)	190–192	80
4	CH3	H2CSi(CH3)2C6H5	C38H62O10N2Si2Ge2Sn (1026)	44.43 (44.35)	6.04 (5.80)	2.72 (2.65)	188–189	70
5	CH3	H2CC6H5	C34H32O10N2Ge2Sn (892)	44.82 (45.90)	5.49 (5.88)	3.07 (2.68)	130–132	65
6	C6H5	H2CC6H5	C44H64O10N2Ge2Sn (1034)	51.05 (50.07)	5.22 (5.20)	2.70 (2.65)	140–142	72
7	p-CH3C6H4	p-CH3C7H6	C48H62O10N2Ge2Sn (1090)	52.73 (52.75)	5.85 (6.0)	2.56 (2.66)	135–137	65
8	C6H5	p-CH3C7H6	C46H56O10N2Ge2Sn (1060)	51.87 (50.95)	5.63 (5.50)	2.63 (2.54)	133–135	65

* White solid compound; soluble in CHCl₃ and DMSO

Table II.  ¹H NMR data^*ab of organotin (IV) derivatives of general formula.

					R^2
Comp.	N(CH2CH2O)3	R^1	CH2	CH	H3C-Si	H2C-Sn	Phenyl
1	2.8(t) [5.7] 3.6(t) [6.0]	Phenyl	2.9	3.8	0.18(s)	0.24(s)	7.0–7.4 (m)
2	2.9(t) [5.7] 3.7(t) [5.5]	Phenyl 0.17(s)	3.4	3.8	0.15(s)	0.26(s)	7.0–7.6 (m)
3	2.7(t) [6] 3.7(t) [5.7]	Phenyl	3.2	3.9	0.14(s)	0.3(s)	6.8–7.2 (m)
4	2.8(t) [5.7] 3.6(t) [5.5]	1.17(d) [7.2]	3.1	3.8	0.13(s)	0.28(s)	7.3–7.5 (m)
5	2.8(t) [5] 3.8(t) [5.5]	1.12(d) [7.1]	3.0	4.1	–	Phenyl 2.5(s)	6.8–7.2 (m)
6	2.9(t) [6] 3.9(t) [6.5]	Phenyl	3.2	4.0	–	Phenyl 2.5(s)	7.3–7.4 (m)
7	2.9(t) [5.4] 3.6(t) [5.6]	Phenyl 2.3(s)	3.1	3.9	–	Phenyl 2.2(s)	6.8–7.2 (m)
8	2.7(t) [5.4] 3.5(t) [5.8]	Phenyl	3.3	3.8	–	Phenyl 2.3(s)	7.0–7.3 (m)

Table III.  ¹³C, ²⁹Si NMR data^ab of organotin (IV) derivatives of general formula.

S.No.		1	2	3	4	5	6	7	8
N(CH2CH2O)3	1	51.4	51.3	51.2	50.9	51.0	50.9	51.4	51.2
	2	56.0	56.8	56.7	56.1	56.1	56.4	56.2	55.9
^1R	i	141.9	140.9	139.8	16.3	16.5	136.9	141.1	133.5
	o	126.7	128.6	128.3	–	–	130.0	127.9	130.0
	m	127.5	129.0	114.8	–	–	125.5	129.0	125.0
	p	132.0	133.9 (21.3)*	162.6	–	–	128.0	135.0 (21.5)*	128.1
^2R	α	142.0	141.2	141.9	142.0	137.1	136.9	137.8	136.0
	^β	133.5	133.4	132.9	133.5	129.9	130.0	129.1	131.0
	γ	128.0	130.1	127.4	129.1	127.5	128.0	128.5	127.3
	δ	128.2	128.5	128.4	129.2	125.5	125.5	125.4 (18.1)*	125.0 (19.2)*
H3C-Si		0.55	0.52	0.04	0.18	–	–	–	–
H2C-Sn		9.28	9.3	9.4	8.99	9.5	9.3	9.8	9.0
R^2-HC		34.9	37.2	36.6	23.7	33.5	36.0	36.6	33.5
H2C		45.8	46.2	39.2	23.9	37.0	39.0	36.8	41.5
COO		179	180.6	179	174.1	172.0	178.5	182	179
^29Si		–	− 3.02	–	− 2.94	–	–	–	–

*Substituents at phenyl is indicated in () at respective carbon

^aIn CDCl₃ at 298K

^bNumbering of carbon atoms is in accordance to the footnote of Table-II.

Table IV.  ^119mSn Mössbauer and ¹¹⁹Sn NMR data (in CDCl₃) of the selected compounds.

Comp.	QS (mms^− 1)	IS (mms^− 1)	ρ (QS/IS)	δ ^119Sn NMR (ppm)
1	3.20	1.22	2.62	− 123.45
2	3.24	1.29	2.51	− 109.66
3	3.22	1.26	2.55	–
4	3.24	1.23	2.63	− 119.78
5	3.27	1.22	2.68	–
7	3.21	1.30	2.46	− 115.40
8	–	–	–	− 105.37

Table V.  Characteristic IR data (cm⁽⁻¹) of organotin(IV) derivatives (1-8).

Comp.	ν(COO)asym	ν(COO)sym	Δν	Δ(Ge(O)	ν(Ge(N)	ν(Sn(C)	ν(SnO)
1	1598	1396	202	901, 832	674	612, 535	430
2	1622	1419	203	903, 840	690	610, 534	431
3	1602	1392	210	900, 830	680	620, 535	440
4	1601	1394	207	911, 828	690	614, 533	426
5	1598	1392	206	900, 852	664	617, 523	451
6	1595	1388	207	899, 821	690	619, 535	450
7	1604	1402	202	895, 825	692	620, 541	417
8	1590	1384	206	898, 817	695	620, 545	460

Table VI.  Mass fragment of a selected compound 2.

Fragments	m/z (Intensity)
[(H2CCH2O)3NGeCH(CH3C6H4)CH2COO]2Sn[CH2Si(CH3)2(C6H5)] 2^+	1180 (n.o)
[(H2CCH2O)3NGeCH(CH3C6H4)CH2COO]Sn[CH2Si(CH3)2C6H5]2^+	798 (3)
[(H2CCH2O)3NGeCH(CH3C6H4)CH2COO]Sn[CH2Si(CH3)2C6H5]^+	649 (2)
[(H2CCH2O)3NGeCH(CH3C6H4)CH2COOSn]^+	502 (4)
[(H2CCH2O)3NGeCH(CH3C6H4)CH2]^+	458 (5)
[(CH2CH2O)3NGeCH(C6H4CH3)CH2COOH]^+	383 (15)
[Sn(CH2Si(CH3)2C6H5)2]^+	418 (14)
[(CH2CH2O)3NGe]^+	220 (100)
[Sn(CH2Si(CH3)2C6H5)]^+	269 (4)
[SnCH2SiCH3]^+	177 (15)
[CH(C6H4CH3)CH2COO]^+	162 (60)
[(CH2CH2O)NGeH(CH2)2]^+	160 (18)
[(CH2CH2O)3N]^+	146 (50)
[N(CH2CH2)2O]^+	86 (50)
[SnH]^+	121 (10)
[Sn]^+	120 (15)

Table VII.  In vitro antileishmanial activity data for compounds (1–8).

Compound	IC50 (μg/ml)
1	12.15
2	1.30
3	Inactive
4	6.00
5	12.25
7	12.25
8	12.25
Petamidine (Standard Drug)	2.56