sintesis tiga turunan...
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Sintesis Tiga Turunan 4-Nitroindola-3-karboksaldehida
Dosen Pembimbing :Prof. Mardi Santoso, Ph.D
Eka Dewi Fitriana1412 100 044
Jurusan KimiaFakultas Matematika dan Ilmu Pengetahuan AlamInstitut Teknologi Sepuluh Nopember Surabaya
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Outline
Pendahuluan1.
Metodologi, Hasil dan Pembahasan2.
Kesimpulan3.
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Pendahuluan
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Kanker
Latar Belakang
Yayasan Kanker Indonesia. 2006. Informasi Dasar tentang Kanker
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Latar Belakang
WHO, 2005International Agency for Research on Cancer, 2013.
2008
7,6 juta
2012
8,2 juta
Jantung &pembuluh
darah
Penyakitmenularibu-anak
Kanker Lain-lain Kecelakaan Saluranpernafasan
Diabetes
0%5%
10%15%20%25%30%35%
Penyebab Kematian Terbesar di Dunia Tahun 2005
7,9%
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Latar Belakang
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Cruciferae (Brassica)
IC50 = 52 µMMCF-7
Brew dkk., 2006. J. Cancer 118: 857-868.
(1)
Latar Belakang
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Nguyen dkk., 2010. J. Chemico-Biological Interaction. 186:255-266.
Latar Belakang
IC50 = 52 µMMCF-7
(1)
Indola-3-karbinol
IC50 = 0,05 µMMCF-7
(2)
1-Benzilindola-3-karbinol
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Rahmayanti, 2014. Tesis, S2 Kimia. Institut Teknologi Sepuluh Nopember Surabaya
Latar Belakang
IC50 = 10,3 mMHepG2
(3a)
3-Hidroksi-3-(1H-pirol-2-il)indolin-2-ona
IC50 = 0,5 mMHepG2
(3b)
3-Hidroksi-5-nitro-3-(1H-pirol-2-il)indolin-2-ona
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Latar Belakang
Wu dkk., 2011. J. Medchem. 54: 2668-2679.
(4a) (4b) (4c)
IC50 = 0,045 µMH460
IC50 = 0,250 µMH460
IC50 = 0,037 µMH460
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Latar Belakang
Wu dkk., 2011. J. Medchem. 54: 2668-2679.
(4d) (4e) (4f)
IC50 = 0,112 µMH460
IC50 = 0,100 µMH460
IC50 = 0,019 µMH460
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Latar Belakang
Wu dkk., 2011. J. Medchem. 54: 2668-2679.
(4f) (4g)
IC50 = >31,6 µMH460
IC50 = >31,6 µMH460
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Latar Belakang
(5)
(8)
(7)(6)
4-Nitroindola-3-karboksaldehida
1-(3-Klorobenzil)-4-nitroindola-3-karbaldehida
[1-(3-Klorobenzil)-4-nitroindola-3-il]metanol
Bis(1-(3-klorobenzil)-4-nitroindola-3-il)metana
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Latar Belakang
(6)
(7)
(5)(9)
(8)
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Permasalahan
(5)
(8)
(7)(6)
??
?
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Tujuan
(8)
(6) (7)
(5)
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Tahapan Penelitian
Sintesis 1-(3-Klorobenzil)-4-nitroindola-3-karbaldehida (6)
Sintesis [1-(3-Klorobenzil)-4-nitroindola-3-il]metanol (7)
Sintesis Bis(1-(3-klorobenzil)-4-nitroindola-3-il)metana(8)
T.1
T.2
T.3
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Metodologi, Hasil dan Pembahasan
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4-Nitroindola-3-karboksaldehida (5)
(0,20 g; 1,05 mmol)
Natrium hidroksida(0,084 g; 2,10 mmol)
-dilarutkan dalam asetonitril (15 mL)
-diaduk pada suhu kamar selama 60 menit
3-Klorobenzil bromida (9)(144,43 µL; 1,10 mmol)
Hasil reaksi 1
T.1
-diaduk lebih lanjut pada suhu kamar selama
120 menit (jalannya reaksi dipantau dengan KLT)
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30’ 90’ 120’
1 2 3 1 2 3 1 2 3
Keterangan :1 = 4-nitroindola-3-karboksaldehida (5)2 = hasil reaksi3 = 3-klorobenzil bromida (9)
Eluen :n-heksana ; etil asetat (5:2)
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4-Nitroindola-3-karboksaldehida (5)
(0,20 g; 1,05 mmol)
Natrium hidroksida(0,084 g; 2,10 mmol)
-dilarutkan dalam asetonitril (15 mL)
-diaduk pada suhu kamar selama 60 menit
3-Klorobenzil bromida (9)(144,43 µL; 1,10 mmol)
Hasil reaksi 1
-diaduk lebih lanjut pada suhu kamar selama
Hasil reaksi 2
-ditambah dengan akuades dingin (15 mL)
-diekstrak dengan diklorometana (3x15 mL)
Fasa organik Fasa air
-dikeringkan dengan MgSO4 anhidrat
-diuapkan dengan rotary evaporator
1-(3-Klorobenzil)-4-nitroindola-3-karbaldehida (6)*
T.1
120 menit (jalannya reaksi dipantau dengan KLT)
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Keterangan eluen :a = n-heksana : kloroform (5:3)b = n-heksana : etil asetat (5:2)c = n-heksana : etil asetat (5:4)
cba
Titik Leleh : 177°C
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Spektrum 1H-NMR 1-(3-Klorobenzil)-4-nitroindola-3-karbaldehida (6) hasil sintesis
Pergeseran kimia (ppm)
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Spektrum 13C-NMR 1-(3-Klorobenzil)-4-nitroindola-3-karbaldehida (6) hasil sintesis
CHCl3
Pergeseran kimia (ppm)
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Spektrum infra merah1-(3-Klorobenzil)-4-nitroindola-3-karbaldehida (6) hasil sintesis
Bilangan gelombang (cm-1)
Pre
sen
tase
tra
nsm
itan
(%
)
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Spektrum massa (APCI)1-(3-Klorobenzil)-4-nitroindola-3-karbaldehida (6) hasil sintesis
m/z
Kel
imp
ahan
rel
atif
(%
)
m/z = 314,7
M+
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1-(3-Klorobenzil)-4-nitroindola-3-karbaldehida (6)
(0,030 g; 0,95 mmol)
Natrium borohidrida(0,018 g; 4,73 mmol)
-dilarutkan dalam etanol (20 mL)
-diaduk pada suhu kamar selama 90 menit
(jalannya reaksi dipantau dengan KLT)
T.2
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30’ 90’
1 2 1 2
Keterangan :1 = 1-(3-klorobenzil)-4-nitroindola-3-
karbaldehida (6)2 = hasil reaksi
Eluen :n-heksana ; etil asetat (5:2)
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1-(3-Klorobenzil)-4-nitroindola-3-karbaldehida (6)
(0,030 g; 0,95 mmol)
Natrium borohidrida(0,018 g; 4,73 mmol)
-dilarutkan dalam etanol (20 mL)
-diaduk pada suhu kamar selama 90 menit
Hasil reaksi
(jalannya reaksi dipantau dengan KLT)
-ditambah aseton (1,04 mL; 14,19 mmoL)-diuapkan pelarutnya sehingga hampir kering
-ditambah larutan natrium hidroksida 10% (7,6 mL)-diuapkan pelarutnya dengan rotary evaporator
-disaring
Endapan Fasa air
-dicuci dengan akuades
-dikeringkan dalam desikator
[1-(3-Klorobenzil)-4-nitroindola-3-il]metanol (7)*
T.2
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Keterangan eluen :a = n-heksana : kloroform (1:4)b = n-heksana : diklorometana (1:4)c = n-heksana : etil asetat (1:4)
Titik Leleh : 112-113°C
cba
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Spektrum 1H-NMR [1-(3-Klorobenzil)-4-nitroindola-3-il]metanol (7) hasil sintesis
Pergeseran kimia (ppm)
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Spektrum 13C-NMR [1-(3-Klorobenzil)-4-nitroindola-3-il]metanol (7) hasil sintesis
Pergeseran kimia (ppm)
CHCl3
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Perbandingan data 1H-NMR turunan 4-nitroindola-3-karboksaldehida (6-7) (dalam ppm)
(6) (7)
Proton Hasil Sintesis (6) Hasil Sintesis
(7)
OH - 2,60 (s,1H)
CH2OH - 4,90 (s,2H)
CH2Ar 5,40 (s,2H) 5,38 (s,2H)
ArH 6,99-8,14
(m,8H)
6,93-7,98
(m,8H)
CHO 10,42 (s,1H) -
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Perbandingan data 13C-NMR turunan 4-nitroindola-3-karboksaldehida (6-7) (dalam ppm)
Karbon Hasil Sintesis
(6)
Hasil Sintesis
(7)
CH2OH - 58,59
CH2Ar 51,00 50,01
ArC 117,36
118,54
135,46
136,41
139,15
142,74
115,70
119,53
135,09
138,11
139,41
142,60
ArCH 117,12
120,30
122,71
125,15
127,24
129,17
130,74
138,01
116,55
118,55
121,21
124,91
126,92
128,55
130,48
132,96
CHO 187,68 -
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Spektrum infra merah [1-(3-Klorobenzil)-4-nitroindola-3-il]metanol (7)
hasil sintesis
Bilangan gelombang (cm-1)
Pre
sen
tase
tra
nsm
itan
(%
)
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Spektrum massa (APCI) [1-(3-Klorobenzil)-4-nitroindola-3-il]metanol (7) hasil sintesis
m/z
Kel
imp
ahan
rel
atif
(%
)
m/z = 316,7
[M+Na-H]+ = 338,7
[M+Na-H]+
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[1-(3-Klorobenzil)-4-nitroindola-3-il]metanol (7)
(0,10 g; 0,17 mmol)
PTSA (21)(0,05 g; 0,26 mmol)
T.3
-dilarutkan dalam diklorometana (7 mL)
-diaduk pada suhu kamar selama 6,5 jam
(jalannya reaksi dipantau dengan KLT)
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30’ 90’
Keterangan :1 = [1-(3-klorobenzil)-4-nitroindola-3-il]
metanol (7)2 = hasil reaksi
Eluen :n-heksana ; etil asetat (5:2)
1 2 1 2 1 2 1 2 1 2 1 2
3 jam 3,5 jam 4,5 jam 6,5 jam
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[1-(3-Klorobenzil)-4-nitroindola-3-il]metanol (7)
(0,10 g; 0,17 mmol)
PTSA (21)(0,05 g; 0,26 mmol)
Hasil reaksi
dengan KLT dan uji titik leleh
T.3
-dilarutkan dalam diklorometana (7 mL)
-diaduk pada suhu kamar selama 6,5 jam
(jalannya reaksi dipantau dengan KLT)
-diuapkan pelarutnya dengan rotary evaporator-dimurnikan dengan KLT preparatif,uji kemurnian
Bis(1-(3-klorobenzil)-4-nitroindola-3-il]metana (8)*
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0,095 g
Keterangan eluen :a = n-heksana : kloroform (4:2)b = n-heksana : etil asetat (5:2)c = n-heksana : diklorometana (1:2)
c
B
a
Titik Leleh : 165-166°C
0,022 g
A
b
A
Eluen :n-heksana ; etil asetat (5:2)
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Spektrum 1H-NMR Bis(1-(3-klorobenzil)-4-nitroindola-3-il)metana (8) hasil sintesis
Pergeseran kimia (ppm)
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Spektrum 13C-NMR Bis(1-(3-klorobenzil)-4-nitroindola-3-il)metana (8) hasil sintesis
Pergeseran kimia (ppm)
CHCl3
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Proton Hasil Sintesis (6) Hasil Sintesis
(7)
Hasil Sintesis
(8)
OH - 2,60 (s,1H) -
CH2OH - 4,90 (s,2H) -
ArCH2Ar - - 4,46 (s,2H)
CH2Ar 5,40 (s,2H) 5,38 (s,2H) 5,24 (s,2H)
ArH 6,99-8,14
(m,8H)
6,93-7,98
(m,8H)
6,87-7,67
(m,8H)
CHO 10,42 (s,1H) - -
(8)(6) (7)
Perbandingan data 1H-NMR turunan
4-nitroindola-3-karboksaldehida (6-8) (dalam ppm)
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Karbon Hasil Sintesis
(6)
Hasil Sintesis
(7)
Hasil Sintesis
(8)
ArCH2Ar - - 25,25
CH2OH - 58,59 -
CH2Ar 51,00 50,01 49,92
ArC 117,36
118,54
135,46
136,41
139,15
142,74
115,70
119,53
135,09
138,11
139,41
142,60
114,73
119,61
134,94
138,51
139,13
143,63
ArCH 117,12
120,30
122,71
125,15
127,24
129,17
130,74
138,01
116,55
118,55
121,21
124,91
126,92
128,55
130,48
132,96
115,36
117,20
120,70
124,81
126,77
128,29
130,38
132,10
CHO 187,68 - -
Perbandingan data 13C-NMR turunan
4-nitroindola-3-karboksaldehida (6-8) (dalam ppm)
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Spektrum infra merah Bis(1-(3-klorobenzil)-4-nitroindola-3-il)metana (8)
hasil sintesis
Pre
senta
se t
ran
smit
an (
%)
Bilangan gelombang (cm-1)
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Spektrum massa (APCI) Bis(1-(3-klorobenzil)-4-nitroindola-3-il)metana (8)
hasil sintesis
m/z
Kel
imp
ahan
rel
atif
(%
)
[M+NH4-H]+ = 606,4
m/z = 585,4,6
[M+NH4-H]+
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Kesimpulan
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Kesimpulan
(5)
(9)
(6)
Rendemen = 96%
(7)
(8)
Rendemen = 95%
Rendemen = 40%
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Terima Kasih
Drs. Agus Wahyudi, MS. Ketua Sidang
Prof. Mardi Santoso, Ph.D. Pembimbing
Dr. Hendro Juwono, M.Si. Penguji
Prof. Dr. Didik Prasetyoko, MSc. Penguji
Adi Setyo Purnomo, M.Sc., Ph.D. Penguji
Ibu Lidia UNAIR (Analis NMR)
Bapak Kaliawan POLINEMA (Analis LCMS APCI)
Mas Erfan ITS (Analis FTIR)
DP2M DIKTI Hibah Penelitian
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(6)
(9)
(5)
Mekanisme reaksi pembentukan 1-(3-Klorobenzil)-4-nitroindola-3-karbaldehida (6) hasil sintesis
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Mekanisme reaksi pembentukan [1-(3-Klorobenzil)-4-nitroindola-3-il]metanol (7) hasil sintesis
(6)
(7)
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Mekanisme reaksi pembentukanBis(1-(3-klorobenzil)-4-nitroindola-3-il)metana (8) hasil sintesis
(7)
(8)
(23)
(7)
(21)
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Spektrum 1H-NMR 1-(3-Klorobenzil)-4-nitroindola-3-karbaldehida (6) hasil sintesis
Pergeseran kimia (ppm)