(This question paper consists of 6 questions on 8 printed pages) (Kertas soalan ini mengandungi 6 soalan dalam 8 halaman yang dicetak)

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1 UIVERITY F MALAYA UIVERITI MALAYA EXAMIATI FR TE DEGREE F BACELR F CIECE PEPERIKAA IJAZA ARJAA MUDA AI ACADEMIC EI 2011/2012 : EMETER 2 EI AKADEMIK 2011/2012 : EMETER 2 CE2323 : MEDICIAL CEMITRY KIMIA UBATA June 2012 Jun 2012 TIME : 2 hours MAA : 2 jam ITRUCTI T CADIDATE : ARAA KEPADA CAL : This paper consists of ection A and B. Kertas soalan ini mengandungi Bahagian A dan B. Answer the questions according to the instructions given in each section. Jawab soalan mengikut arahan yang diberikan dalam setiap bahagian. (This question paper consists of 6 questions on 8 printed pages) (Kertas soalan ini mengandungi 6 soalan dalam 8 halaman yang dicetak)

2 CE2323/02 ECTI A (50 MARK) BAAGIA A (50 MARKA) Answer ALL questions. Jawab EMUA soalan. 1. Explain any two (2) of the following terms: Terangkan mana-mana dua (2) daripada terma-terma yang berikut: (a) (d) Bacteriostatic Bakteriostatik Antagonist Antagonis tructure-activity relationship Perhubungan struktur-aktiviti Drug extension Drug pertambahan (6 marks/markah) 2. (a) Explain the selectivity of anti-bacterial agents against bacterial cells. Bincangkan selektiviti agen anti-bakteria terhadap sel bakteria. (4 marks/markah)

3 CE2323/03. Consider the following sulpha drugs P, Q and R. ubsequently, arrange P, Q and R in order of ascending toxicity. Provide an explanation that justifies your answer. Pertimbangkan drug-drug sulfa P, Q dan R yang berikut. eterusnya, susunkan ketoksikan P, Q dan R dalam tertib menaik. Berikan justifikasi anda. 2 2 (P) (Q) 2 (R) 3 C C 3 By using a suitable diagram, explain how staphylococci, pneumococci and gonococci can acquire resistance towards sulphonamides. Dengan menggunakan gambarajah yang sesuai, terangkan bagaimana staphylococci, pneumococci and gonococci dapat membina rintangan terhadap sulfonamida. (4 marks/markah)

4 CE2323/04 (d) Two molecules are presented below. Which one is a better penicillin analogue? Explain your choice. Dua molekul tertera di bawah. Yang manakah merupakan analog penisilin yang lebih baik? Jelaskan pilihan anda. () C 3 C 3 C R R' (T) C 3 C 3 C (e) By means of a reaction mechanism, show how the five-membered thiazolidine ring in penicillin (U) can be converted into six membered dihydrothiazine ring in cephalosporins (V). Dengan menggunakan mekanisme kimia, tunjukkan bagaimana gelang lima thiazolidina dalam penisilin (U) dapat diubah kepada gelang enam dihidrothiazina dalam selfalosporina (V). R C 3 C 3 C R C 3 C (U) (V) (10 marks/markah) 3. (a) ne of the strategies employed in development of morphine analogues is rigidification. Discuss the advantages of such strategy. alah satu strategi bagi pembentukan analog morfina adalah ketegangan. Bincangkan kebaikan-kebaikan yang boleh diperolehi melalui strategi tersebut. (4 marks/markah)

5 CE2323/05 how a reaction scheme for the synthesis of following drug (W) by using a suitable precursor. Tunjukkan skema tindak-balas bagi sintesis drug (W) yang berikut dengan menggunakan bahan pemula yang sesuai. 3 C 2 C 2 C (W) (4 marks/markah) Predict the analgesic activity of drug (X) in comparison with drug (W). Ramalkan aktiviti analgesik drug (X) berbanding dengan drug (W). C 2 (X) (8 marks/markah)

6 CE2323/06 ECTI B (50 MARK) BAAGIA B (50 MARKA) Answer ALL questions. Jawab EMUA soalan. 4. (a) Define the term therapeutic index Takrifkan therapeutic index Explain why a higher therapeutic index is preferable compared to a lower one. Jelaskan mengapa therapeutic index yang tinggi lebih utama daripada yang lebih rendah. 5. (a) Besides receptor, what are the other principle protein targets with which drugs can interact? elain reseptor, apakah protein sasaran utama yang boleh berinteraksi dengan drug? Potency and efficacy are two different concepts and are not interchangable. What is meant by potency and what is efficacy? Potensi dan efikasi adalah dua konsep yang berbeza dan tidak boleh bertukar ganti. Apakah yang dimaksudkan dengan potensi dan apakah dia efikasi?

CE2323/07 The graph below is dose response curve illustrating the characteristics of antagonists. In a short paragraph (not more than 10 words), explain what the graph means.

7 CE2323/07 The graph below is dose response curve illustrating the characteristics of antagonists. In a short paragraph (not more than 10 words), explain what the graph means. Geraf dibawah ialah lengkuk dos-gerakbalas yang mengambarkan ciri antagonis. Dalam satu perenggan ringkas (tidak melebihi 10 perkataan), jelaskan maksud geraf tersebut. (10 marks/markah) 6. (a) In udlicky s chemoenzymatic azide-free synthesis of oseltamivir, the allylic alcohol (A) underwent Dauben-Michno oxidation to give the intermediate (B). Draw the stucture of B. Dalam sintesis kemoenzimatik azida-bebas oseltamivir oleh udlicky, alkohol alilik (A) mengalami pengoksidaan Dauben-Michno untuk menghasilkan bahan perantaraan (B). Lukis stuktur (B).

CE2323/08 Fukuyama s strategy for the synthesis of (-)-oseltamivir is to begin with the reaction between dihydropyridine (C) and acrolein to give the bicyclic aldehyde (D). Give the structure of (D).

Trost and Zhang synthesised oseltamivir in 8 steps starting from a lactone. In their synthesis sequence, they reacted the aziridine (E) to give the ester (F).

8 CE2323/08 Fukuyama s strategy for the synthesis of (-)-oseltamivir is to begin with the reaction between dihydropyridine (C) and acrolein to give the bicyclic aldehyde (D). Give the structure of (D). trategi Fukuyama dalam sintesis (-)-oseltamivir bermula dengan tindak balas diantara dihidropiridin (C) and akrolein untuk menghasilkan ldehid bisiklik (D). Berikan stuktur (D). Trost and Zhang synthesised oseltamivir in 8 steps starting from a lactone. In their synthesis sequence, they reacted the aziridine (E) to give the ester (F). Give the structure of (F) and show the mechanism for this transformation. Trost dan Zhang mensintesis oseltamivir dalam 8 langkah bermula dengan lakton. Dalam sintesis tersebut, mereka menindak balaskan aziridin (E) untuk menghasilkan ester (F). Berikan struktur (F) dan tunjukkan mekanisme bagi transformasi tersebut. (10 marks/markah) ED TAMAT

(Kertas soalan ini mengandungi 8 soalan dalam 9 halaman yang dicetak) (This question paper consists of 8 questions on 9 printed pages)

(Kertas soalan ini mengandungi 8 soalan dalam 9 halaman yang dicetak) (This question paper consists of 8 questions on 9 printed pages) UIVERITI MALAYA UIVERITY F MALAYA PEPERIKAA IJAZA ARJAA MUDA AI EXAMIATI FR TE DEGREE F BACELR F CIECE EI AKADEMIK 2014/2015 : EMETER 2 ACADEMIC EI 2014/2015 : EMETER 2 CE2323 : KIMIA UBATA MEDICIAL CEMITRY