QuestionQuestion

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.

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1) Explain why you picked this compound.
Ans: I selected compound Afatinib because it matches with the given criteria such as it is newly approved anticancer agent and also a current topic of interest. The structure of afatinib has more than six carbons, more than two different functional groups such as amine, amide, ether, halogen, quanazoline, ene etc, and also have one chiral carbon in its structure.

2) Give the compound’s use
Ans: Afatinib is novel anticancer agents currently used as first-line treatment of patients with distinct types of metastatic (EGFR mutation positive) non-small cell lung carcinoma (NSCLC) and recently approved by US –FDA.1, 2, It is available in various brands like Gilotrif, Giotrif, Tomtovok, Tovok etc. This drug is formulated in its salt form as afatinib dimaleate. It acts as an irreversible covalent inhibitor of the receptor tyrosine kinases epidermal growth factor receptor (EGFR) and erbB-2 (HER2).3, 4...
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