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Structure Modification of Ethyl p-methoxycinnamate Isolated from Kaempferia galanga Linn. and Citotoxicity Assay of The Products on WiDr Cells Ekowati, Juni; Rudyanto, Marcellino; Sasaki, Shigeru; Budiati, Tutuk; Sukardiman, .; Hermawan, Adam; Meiyanto, Edy
Indonesian Journal of Cancer Chemoprevention Vol 1, No 1 (2010)
Publisher : Indonesian Research Gateway

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (4.399 KB)

Abstract

Ethyl p-methoxycinnamate, major ingredient of Kaempferia galanga rhizome, have been reported not only has analgesic – anti inflammatory activities like NSAIDs which inhibited cyclooxygenase, but also inhibit tumor cell proliferation in specimen of mouse epidermis. Therefore, it will be interesting to carry out  synthetic studies on the derivates of ethyl  p-methoxycinnamate and searching their citotoxic activity on WiDr cell. We wish to report of structure modification on carboxyl moiety of  ethyl p-methoxycinnamate  and  evaluation on their citotoxic activity  on WiDr cell. Isolation of ethyl p-methoxycinnamate from Kaempferia galanga rhizome was carried out by percolation with ethanol 96% as solvent. Hydrolysis of ethyl p-methoxycinnamate in basic condition was performed to obtain p-methoxycinnamic acid. Preparation of some thiourea derivates of ethyl  p-methoxycinnamate was carried out  by microwave irradiation. Citotoxicity assay was carried out by MTT method for 48 h.   Modification  of  carboxyl  group  of  ethyl  p-methoxycinnamate to its thiourea form could be carried out by microwave irradiation gave; (E)-3-(4-methoxyphenyl)-N-(phenylcarba- mothioyl)acrylamide (50%); (E)-3-(4-methoxyphenyl)-N-(4-methoxyphenylcarbamothi- oyl)acrylamide (26%) and (E)-3-(4-methoxyphenyl)-N-(4-methylphenylcarbamothioyl) acrylamide (54%), yield calculated for 2 step from the acid chloride. All compounds showed no citotoxic effect on WiDr cell at 48 h incubation.
Synthesis Octyl p-Methoxycinnamate as Sunblock by Transesterification Reaction with the Starting Material Ethyl p-methoxycinnamate Suzana, .; Irawati, Nunuk; Budiati, Tutuk
Indonesian Journal of Cancer Chemoprevention Vol 2, No 2 (2011)
Publisher : Indonesian Research Gateway

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Abstract

Synthesis  octyl  p-methoxycinnamate  substance  as  sunblock,  has  been  done  by transesterification  reaction.  The  starting  material  of  the  reaction  was  ethyl  p-methoxycinnamate  isolated  from  Kaempferia  galanga  L.The  transesterification  reaction  was carried out by reacting  ethyl p-methoxycinnamate with octanol. The product was identified by UV-VIS,Infra Red and Mass Spectroscopy. The result of measurements on erythemic %T at various concentrations demonstrate that octyl p-methoxycinnamate is applicable as a sunblock compound. Key  words  :  octyl  p-methoxycinnamate,  transesterification,  ethyl  p-methoxycinnamate,  sunblock
Pengaruh Gugus Metil pada Posisi Para dari Turunan 2-(P-Klorofenil)-Kuinazolin-4(3h)-On terhadap Aktivitas Analgesik pada Mencit Soeliono, Ivonne; Budiati, Tutuk; Tamayanti, Wahyu Dewi
Jurnal Farmasi Sains dan Terapan Vol 6, No 1 (2019)
Publisher : Jurnal Farmasi Sains dan Terapan

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.33508/jfst.v6i1.2006

Abstract

This study has evaluated analgesic activity of 3-benzylideneamino-2-(p-chlorophenyl)-quinazoline-4(3H)-one and 3-(4-methylbenzylideneamino)-2-(p-chlorophenyl)-quinazoline-4(3H)-one. The purposes of this study were to measure analgesic activity, to compare their analgesic potency against mefenamic acid, and to determine the effect of methyl substituent addition on para position of 3-benzylideneamino-2-(p-chlorophenyl)-quinazoline-4(3H)-one toward analgesic activity in mice. Analgesic activity evaluation was performed in mice using writhing test method with acetic acid as pain inducer. The significance difference of writhing frequencies between each group was tested using one-way ANOVA followed by Tukey HSD test as a post-hoc test. The statistic comparison results showed that the synthesized drug and the reference compound had an analgesic activity, in which the synthesized drug had the same analgesic potency with mefenamic acid on the same dosage, and the addition of methyl substituent on para position of 3-benzylideneamino-2-(p-chlorophenyl)-quinazoline-4(3H)-one did not lead to the increase of analgesic activity in mice.
Perbandingan Sintesis Antara Senyawa 2'-Nitrokhalkon dan 2,4-Dimetoksi-2'-Nitrokhalkon dengan Bantuan Iradiasi Gelombang Mikro Putri, Navyanti Firda; Soewandi, Ami; Budiati, Tutuk
Jurnal Farmasi Sains dan Terapan Vol 6, No 2 (2019)
Publisher : Jurnal Farmasi Sains dan Terapan

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (350.787 KB) | DOI: 10.33508/jfst.v6i2.2238

Abstract

The purposes of this research were to find out the influence of a methoxy group to the result percentage reaction and synthesize derivatives of chalcone from derivatives of acetophenone and 2-nitrobenzaldehyde. The purity analysis of the synthesized result was determined by melting point assay and thin layer chromatography, while the identification of the structure was determined by spectrophotometry, infrared pectrophotometry and nuclear magnetic resonance (H-NMR). In the synthesis of compounds formed 3-hydroxy-3- (2-nitrophenyl)-1-fenilpropan-1one and 3-hydroxy-1-(2,4-dimetoksifenil)propan-1-on. The synthesis results obtained an average percentage yield synthesis of 3-hydroxy-3-(2-nitrophenyl)-1-phenylpropan-1-on with the conventional method and with the aid of microwave irradiation amounted to 60.45% and 32.36%. The percentage results of the synthesis for compounds 3-hydroxy-1-(2,4-dimethoxyphenyl)-3-(2-nitrophenyl)propan-1-on with the conventional method and with the aid of microwave irradiation amounted to 11.51% and 5.57%. The influence of methoxy groups can decrease the reactivity of acetophenone.
Sintesis dan Uji Aktivitas Antioksidan Senyawa 4,4’-dinitrodibenzalaseton dengan Metode DPPH Jessica, Jessica; Budiati, Tutuk; Caroline, Catherine
Jurnal Farmasi Sains dan Terapan Vol 8, No 2 (2021): Oktober
Publisher : Jurnal Farmasi Sains dan Terapan

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.33508/jfst.v8i2.2761

Abstract

Senyawa dibenzalaseton dan turunannya yaitu senyawa 4,4’-dinitrodibenzalaseton adalah salah satu jenis antioksidan sintetik dan tergolong ke dalam analog Kurkumin. Senyawa Dibenzalaseton dan 4,4’-dinitrodibenzalaseton merupakan senyawa yang dapat menangkal radikal bebas yang disintesis melalui reaksi kondensasi Claisen-Schmidt dengan perbandingan Benzaldehida/4-nitrobenzaldehida dan Aseton adalah 2:1 mEq dengan menggunakan katalis NaOH. Hasil sintesis dilakukan uji kemurnian dan uji identifikasi struktur dengan menggunakan spektroskopi Inframerah. Persentase rendemen hasil sintesis dibenzalaseton dan 4,4’-dinitrodibenzalaseton adalah sebesar 92,30% dan 96,70%. Uji aktivitas antioksidan dilakukan dengan metode DPPH, dengan senyawa Kurkumin dan Vitamin C sebagai pembanding dan hasilnya dinyatakan dengan nilai IC50. Perolehan rata-rata nilai IC50 dari senyawa dibenzalaseton, 4,4’-dinitrodibenzalaseton, kurkumin dan vitamin C secara berturut-turut adalah 66 mM, 1,6 mM, 0,074 mM, dan 0,0846 mM. Hal ini menunjukkan bahwa aktivitas antioksidan senyawa 4,4’-dinitrodibenzalaseton lebih besar dibanding dengan senyawa dibenzalaseton. Nilai IC50 yang rendah dari senyawa kurkumin menunjukkan bahwa aktivitas antioksidan yang dimiliki oleh Kurkumin lebih tinggi dari senyawa hasil sintesis. Potensi antioksidan yang dihasilkan oleh dan 4,4’-dinitrodibenzalaseton terhadap vitamin C adalah sebesar 5,28%.
Sintesis dan Uji Aktivitas Senyawa 1-Benzil-3-benzoilurea Tersubstitusi Bromo, Kloro, Floro dan Triflorometil pada posisi para sebagai Agen Antiproliferatif Farida Suhud; Siswandono Siswandono; Tutuk Budiati
MPI (Media Pharmaceutica Indonesiana) Vol. 1 No. 3 (2017): JUNE
Publisher : Fakultas Farmasi, Universitas Surabaya

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (745.845 KB) | DOI: 10.24123/mpi.v1i3.266

Abstract

Sintesis dan uji aktivitas 1-benzil-3-benzoilurea tersubstitusi F, Cl, Br dan CF3 pada posisipara sebagai agen antiproliferatif telah dilakukan. Tujuan dari studi ini untuk membandingkanaktivitas sebagai agen antiproliferatif senyawa 1-benzil-3-benzoilurea dengan substituen golonganhalogen. Untuk mencapai tujuan tersebut uji aktivitas secara in-silico terhadap reseptor 1-UWH diprediksidengan Molegro Virtual Docker (MVD) 5 dan hidroksiurea digunakan sebagai pembanding.Selanjutnya uji aktivitas secara in-vitro terhadap kultur sel MCF-7 dilakukan dengan MTT-assay. Hasildidapatkan senyawa 1-benzil-3-(4-CF3-benzoil)urea lebih poten dibandingkan yang lain. Sangatdirekomendasikan untuk dilakukan prediksi bioavailabilitas dan toksisitas serta uji lebih lanjut senyawa1-benzil-3-(4 CF3-benzoil)urea sebagai calon obat dengan aktivitas antiproliferatif.
Synthesis and Molecular Docking Studies of N’-benzoylsalicylhydrazide derivatives as antituberculosis through InHA enzym inhibition Harry Santosa; Galih Satrio Putra; Tegar Achsendo Yuniarta; Tutuk Budiati
Indonesian Journal of Pharmacy Vol 29 No 4, 2018
Publisher : Faculty of Pharmacy Universitas Gadjah Mada, Yogyakarta, Skip Utara, 55281, Indonesia

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (1120.908 KB) | DOI: 10.14499/indonesianjpharm29iss4pp198

Abstract

The specific aims of this study is to synthesize and to study the possible mechanism of N’-benzoylsalicylhydrazide derivatives as an antituberculosis agent through InhA (Enoyl acyl carrier protein reductase) inhibition using in silico method. Five analogues of N’-benzoylsalicylhydrazide were synthesized using microwave irradiation from methyl salicylate as starting material, which yielded 80-90% product on average. This indicates a considerable improvement in terms of effectivity and efficiency, compared to the more conventional method using reflux condition. Character-ization of the compounds were subsequently carried out by UV, FTIR, 1H-NMR, 13C-NMR spectroscopy, which confirmed that the compounds had been successfully synthesized. Ultimately, molecular docking was performed using Molegro Virtual Docker (MVD) on the active site of InhA enzyme to predict the activity of the compounds. The results showed that all compounds performed comparatively well against N-(4-Methylbenzoyl)-4-benzylpiperidine as the native ligand and also yielded lower docking score than isoniazide (INH). From this study it can be concluded that N’-benzoylsalicylhydrazide derivatives could be synthesized using microwave irradiation with good product yield and all of the synthesized analogues are suggested to possess antituberculosis activity via InhA enzyme inhibition. In vitro activity will have to be determined in the future to validate whether N’-benzoylsalicylhydrazide derivatives perform well as a potential antituberculosis agent.
Synthesis, analgesic and anti-inflammatory activities of substituted benzoylthioureas Tutuk Budiati; Suzana .; Siti Surdijati
Indonesian Journal of Pharmacy Vol 21 No 1, 2010
Publisher : Faculty of Pharmacy Universitas Gadjah Mada, Yogyakarta, Skip Utara, 55281, Indonesia

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (261.607 KB) | DOI: 10.14499/indonesianjpharm0iss0pp68-76

Abstract

Three compounds (i.e.  benzoylthiourea,  4-nitrobenzoylthiourea,  and  4-chlorobenzoylthiourea) have  been  synthesized  from  ammonium  thiocyanate, substituted benzoyl chlorides, and ammonia as starting materials. The structures of  sythesized  compounds  were  confirmed  by  means  of  ultra-violet,  infrared, magnetic resonance, and mass spectroscopy. All compounds were evaluated for their  analgesic  and  anti-inflamatory  activities  by  tail-flick  technique  and carragenan-induced  paw  oedema  test  respectively.  Substitution of p-NO2 and p-Cl  group  to  benzoylthiourea  increased  the  analgesic  and  anti-inflamatory activities.  The  two  compounds,  4-nitrobenzoylthiourea  and  4-chlorobenzoylthiourea,  were  significantly  more  potent  as  analgesic  but  their  antiinflamatory actvity was weaker than Na-diclofenac.Keywords: benzoylthioureas, p-Cl dan p-NO2substituents, analgesic and anti-inflamator activities
Design and Molecular Docking Studies of Quinazoline Derivatives as Antiproliferation Anita Puspa Widiyana; Galih Satrio Putra; Luthfi Ahmad Muchlashi; Mellany Ika Sulistyowaty; Tutuk Budiati
JURNAL FARMASI DAN ILMU KEFARMASIAN INDONESIA Vol. 3 No. 2 (2016): JURNAL FARMASI DAN ILMU KEFARMASIAN INDONESIA
Publisher : Universitas Airlangga

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (284.943 KB) | DOI: 10.20473/jfiki.v3i22016.44-48

Abstract

Background: Nowadays, a lot of new active substances as anticancer agents have been developed. One of the protein targets of anticancer is selective cyclooxygenase-2 (COX-2). Selective COX-2 is the regulator of cell proliferation. Objective: In this research, quinazoline derivatives were used to design the anticancer agent through a selective COX-2 inhibition. The potential activity of quinazoline derivatives could be increased by substitution in position 2 and 3 of quinazolinone. Molecular docking of selective COX-2 inhibition was required to predict their antiproliferation activity. Methods: The molecular docking of quinazoline derivatives was carried out using Molegro Virtual Docker (MVD) Ver.5.5. Twenty-one of quinazoline derivatives were docked into selective COX-2 with PDB code 3LN1. The interaction was evaluated based on the re-ranked score comparison between quinazoline derivatives with co-crystallized ligand CEL_682. Celecoxib was used as the reference to this research. Results: The result indicated that 18 of 21 quinazoline derivatives showed the approximately re-ranked score -131.508 to -108.418 kcal/mol. Eight of these 18 new quinazoline derivatives have re-ranked score better than Celecoxib. Conclusions: In conclusion, 8 of the new quinazoline derivatives are feasible to be synthesize and performed their in vitro evaluation.
Synthesis Octyl P-Methoxycinnamate as Sunblock by Transesterification Reaction with the Starting Material Ethyl P- Methoxycinnamate Suzana Suzana; Nunuk Irawati; Tutuk Budiati
Indonesian Journal of Cancer Chemoprevention Vol 2, No 2 (2011)
Publisher : Indonesian Society for Cancer Chemoprevention

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.14499/indonesianjcanchemoprev2iss2pp217-221

Abstract

Synthesis octyl p-methoxycinnamate substance as sunblock, has been done by transesterification reaction. The starting material of the reaction was ethyl p-methoxycinnamate isolated from Kaempferia galanga L.The transesterification reaction was carried out by reacting  ethyl p-methoxycinnamate with octanol. The product was identified by UV-VIS,Infra Red and Mass Spectroscopy. The result of measurements on erythemic %T at various concentrations demonstrate that octyl p-methoxycinnamate is applicable as a sunblock compound.Keywords: octyl p-methoxycinnamate, transesterification, ethyl p-methoxycinnamate, sunblock