Sintesis Senyawa-senyawa Sinamamida dari trans-Asam Sinamat dan Bromoanilin

Yusuf, Moechamad Hikmal Rizky Abi (2025) Sintesis Senyawa-senyawa Sinamamida dari trans-Asam Sinamat dan Bromoanilin. Other thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Sinamamida, salah satu turunan asam sinamat yang berupa amida diketahui memiliki aktivitas anti tuberkulosis, anti kanker, anti diabetes, anti mikroba, dan anti inflamasi sehingga menarik untuk dieksplorasi dalam pengembangan obat baru. Senyawa sinamamida dari kombinasi trans-asam sinamat (1) dengan anilin tersubstitusi dilaporkan memiliki aktivitas antibakteri dan anti kanker. Selain itu, penambahan gugus bromo pada cincin fenil senyawa sinamamida diketahui mampu meningkatkan aktivitas antikanker. Penelitian yang dilakukan berhasil memperoleh senyawa sinamamida baru dari kombinasi tersebut, yakni N-(3-bromofenil)sinamamida (3e) dan N-(4-bromofenil)sinamamida (3f). Sintesis senyawa sinamamida umumnya dilakukan melalui pembentukan asil halida dengan bantuan tionil klorida. Namun, tionil klorida termasuk dalam daftar Chemical Weapons Convention yang penggunaannya dilarang di beberapa negara. Namun dengan mengadaptasi metode esterifikasi shiina, kombinasi anhidrida 2-metil-6-nitrobenzoat (MNBA) (5) dengan 4-(dimetilamino)piridina (DMAP) (6) dilaporkan cukup efektif dalam sintesis senyawa karboksamida. Prinsip metode Shiina adalah transformasi asam karboksilat menjadi anhidrida asam tidak simetri dengan bantuan MNBA (5) dan (DMAP) (6), yang kemudian direaksikan dengan senyawa amina sehingga diperoleh senyawa amida. Senyawa N-(3-bromofenil)sinamamida (3e) berhasil disintesis dengan melibatkan reaksi trans-asam sinamat (1), anhidrida asam 2-metil-6-nitrobenzoat (MNBA) (5), 4-(dimetilamino)piridina (DMAP) (6), 3-bromoanilin (2a) dan diperoleh dengan rendemen 11%. Senyawa N-(4-bromofenil)sinamamida (3f) berhasil disintesis dengan melibatkan reaksi trans-asam sinamat (1), anhidrida asam 2-metil-6-nitrobenzoat (MNBA) (5), 4-(dimetilamino)piridina (DMAP) (6), 4-bromoanilin (2b), dan diperoleh dengan rendemen 35%.
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Cinnamamide, a derivative compound of cinnamic acid in the form of an amide, is known to have anti-tuberculosis, anti-cancer, anti-diabetes, anti-microbial and anti-inflammatory activities, making it interesting to explore in the development of novel drugs. The cinnamamide compounds from a combination of trans-cinnamic acid (1) with substituted aniline has been reported to have antibacterial and anti-cancer activity. Furthermore, the addition of a bromo group to the phenyl ring of cinnamamide compound is known to increase anticancer activity. The research carried out succeeded in obtaining new cinnamamide compounds from this combination, namely N-(3-bromophenyl)cinnamamide (3e) and N-(4-bromophenyl)cinnamamide (3f). The synthesis of cinnamamide compounds is generally carried out through the formation of acyl halides with the help of thionyl chloride. However, thionyl chloride is included in the Chemical Weapons Convention list so its use is prohibited in several countries. However, by adapting the shiina esterification method, the combination of 2-methyl-6-nitrobenzoic anhydride (MNBA) (5) with 4-(dimethylamino)pyridine (DMAP) (6) was reported to be quite effective in the synthesis of carboxamide compounds. The principle of the Shiina method is the transformation of carboxylic acid into asymmetric acid anhydride with the help of MNBA (5) and (DMAP) (6), which is then reacted with an amine compound to obtain an amide compound. The compound N-(3-bromophenyl)cinnamamide (3e) was successfully synthesized by involving the reaction of trans-cinnamic acid (1), 2-methyl-6-nitrobenzoic acid anhydride (MNBA) (5), 4-(dimethylamino)pyridine (DMAP) (6), 3-bromoaniline (2a) and obtained with a yield of 11%. The compound N-(4-bromophenyl)cinnamamide (3f) was successfully synthesized by involving the reaction of trans-cinnamic acid (1), 2-methyl-6-nitrobenzoic acid anhydride (MNBA) (5), 4-(dimethylamino)pyridine (DMAP) (6), 4-bromoaniline (2b), and was obtained in 35% yield.

Item Type:	Thesis (Other)
Uncontrolled Keywords:	Bromoanilin, Esterifikasi shiina, Sinamamida, trans-Asam sinamat
Subjects:	Q Science > QD Chemistry > QD471 Chemical compounds - Structure and formulas
Divisions:	Faculty of Science and Data Analytics (SCIENTICS) > Chemistry > 47201-(S1) Undergraduate Thesis
Depositing User:	Moechamad Hikmal Rizky Abi Yusuf
Date Deposited:	04 Feb 2025 22:31
Last Modified:	04 Feb 2025 22:31
URI:	http://repository.its.ac.id/id/eprint/118167

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