Question

Pick an organic compound – it can be a food or cosmetic ingredient, medicine, pesticide or any other compound that is a current topic of interest (e.g., illegal drugs, new cancer
chemotherapeutic agents). The compound should contain: 1) more than six carbons; 2) more than 2 different functional groups; 3) at least one chiral carbon.

Part 1
1) Explain why you picked this compound.
2) Give the compound’s use
3) Determine the time frame of its discovery or introduction into usage
4) Give the IUPAC name of the compound
5) Provide the structure of the compound, and write the molecular formula
6) Identify all functional groups in the compound ON THE STRUCTURE
7) Identify the chiral carbon(s) present in the compound ON THE STRUCTURE
8) Indicate if the marketed compound is a mixture of stereoisomers or not; if the marketed compound is an enantiomerically pure compound, draw the absolute configuration(s) of any chiral centers if not already present in the structure

Part 2
9) Find the synthesis of the chosen molecule. Highlight and explain at least one reaction in the synthesis.

Solution Preview

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1) Explain why you picked this compound.
Ans: The Abiraterone acetate is selected because it matches as per the given criteria such as it is newly approved anti-prostate cancer agent and it is also a current topic of interest. The structure of abiraterone acetate has more than six carbons, more than two different functional groups such as acetyl, ester, ene, pyridyl, and has six chiral carbons. These all criteria making this molecule special one for investigation.

2) Give the compound’s use
Ans: Abiraterone acetate is a novel anti-prostate cancer agents currently used in the treatment of prostate cancer and recently approved by USFDA.1, 2 This molecule is available under various brand name such as Zytiga, Abirapro, Abretone, Abiratas etc. It is a steroidal antiandrogen, which inhibits the androgen receptors and blocks the synthesis of androgen such as testosterone. It is a regarded as prodrug and biotransformed to its active metabolite as abiraterone. This medicine is commonly used in combination with prednisone in metastatic castration-resistant prostate cancer....

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