Synthesis Of 1,3-di-(6-Bromoindole-3-Carbaldehyde-1-Ylmethyl)Benzene And 1,3-di-(6-Bromoindole-3-Hydroxymethyl-1-Ylmethyl)Benzene

Fadhiilah, Umi (2017) Synthesis Of 1,3-di-(6-Bromoindole-3-Carbaldehyde-1-Ylmethyl)Benzene And 1,3-di-(6-Bromoindole-3-Hydroxymethyl-1-Ylmethyl)Benzene. Undergraduate thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Tumbuhan genus Brassica (kubis, lobak, kembang kol, dan brokoli) telah diketahui mengandung indola-3-karbinol yang menghambat berbagai jenis kanker seperti kanker payudara, kanker prostat, kanker kolorektal, dan kanker getah bening. Uji sitotoksisitas menunjukkan bahwa N-benzilindola-3-karbaldehida dan N-benzilindola-3-karbinol lebih sitotoksik terhadap sel kanker payudara MCF-7 dan MDA-MB-231 dari pada indola-3-karbinol akibat adanya gugus N-benzil. Gugus pensubstitusi hidroksimetil dan aldehida pada posisi C-3 serta bromo pada posisi C-6 cincin indola juga diketahui dapat meningkatkan aktivitas anti-kanker. Sehubungan dengan data tersebut, penelitian yang dilakukan bertujuan untuk mendapatkan 1,3-di-(6-bromoindola-3-karbaldehida-1-ilmetil)benzena yang diperkirakan lebih poten dari pada benzilindola-3-karbaldehida dan 1,3-di-(6-bromoindola-3-hidroksimetil-1-ilmetil)benzena yang diperkirakan lebih poten dari pada benzilindola-3-karbinol. Reaksi 6-bromoindola-3-karboksaldehida, natrium hidrida, dalam asetonitril diperoleh 1,3-di-(6-bromoindola-3-karbaldehida-1-ilmetil)benzena dengan rendemen 93%. Reduksi 1,3-di-(6-bromoindola-3-karbaldehida-1-ilmetil)benzena dengan natrium borohidrida dalam etanol diperoleh 1,3-di-(6-bromoindola-3-hidroksimetil-1-ilmetil) benzena dengan rendemen 92%.

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Brassica genus (cabbage, radish, cauliflower, and broccoli) have been known to contain indole-3-carbinol that can inhibits a variety of cancer such as breast cancer, prostate cancer, colorectal cancer, and cancer of the lymph nodes. Cytotoxicity assay showed that the N-benzilindola-3-karbaldehida and N-benzilindola-3-carbinol is more cytotoxic against breast cancer cell line MCF-7 and MDA-MB-231 of the indole-3-carbinol result of the N-benzyl group. Hydroxymethyl, and aldehyde substituent group at C-3 position and bromo at C-6 position of indole ring is also known to enhance the anti-cancer activity. In connection with such data, research conducted aims to obtain 1,3-di-(6-bromoindola-3-karbaldehida-1-ilmetil)benzena were estimated to be more potent than benzilindola-3-karbaldehida and 1,3-di-(6-bromoindola-3-hydroxymethyl-1-ilmetil)benzene were estimated to be more potent than benzilindola-3-carbinol. Reaction of 6-bromoindola-3-karboksaldehida, sodium hydride, in acetonitrile obtained 1,3-di- (6-bromoindola-3-karbaldehida-1-ilmetil) benzene with 93% of yield. Reduction of 1,3-di- (6-bromoindola-3-karbaldehida-1-ilmetil) benzene with sodium borohydride in ethanol obtained 1,3-di- (6-bromoindola-3-hydroxymethyl-1-ilmetil) benzene with 93% of yield.

Item Type:	Thesis (Undergraduate)
Uncontrolled Keywords:	N-benzilindola-3-karbinol; N-benzilindola-3-karbaldehida; indola-3-karbinol
Subjects:	Q Science > QD Chemistry
Divisions:	Faculty of Mathematics and Science > Chemistry > 47201-(S1) Undergraduate Thesis
Depositing User:	Anis Wulandari
Date Deposited:	02 May 2017 07:55
Last Modified:	02 May 2017 07:55
URI:	http://repository.its.ac.id/id/eprint/41211

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