Question

Description A large percentage of drugs (>60%) are based on natural products that have been isolated from nature. For this assignment, pick a drug that is a natural product or is based on the structure of a natural product. The compound is required to have at least 4 chiral carbons. Students must choose a unique compound. Post the structure of the drug. (1 point) List four functional groups that are in the molecule. (2 points) Identify the chiral carbons and configuration (R or S) for each carbon. (2 points) Describe what the drug is used to treat. (1 point) List the source of the natural product. (2 points) List an interesting fact or why you picked this compound. (1 point) Include reference(s). (1 point)

Answer 1

I have chosen Doxorubicin , which contains total 6 chiral centers. Doxorubicin is a natural product, isolated from the bacterium Streptomyces peucetius var. caesius. This drug is currently using in the treatment of Cancer. The chemical structure is given below. It contains several functional groups, one amine NH2 functional group (represented in blue color) and the functional groups from oxygen represented in red color in the figure. The oxygen molecules forms hydroxy (-OH), Ketone, and ether functionalities.

One amine -NH2 functionality

There are total 5 -OH groups present in the molecule.

Three ketones are present.

and three ether groups are there.

Treatment: (source : pubmed)

Doxorubicin has been used successfully to produce regression in disseminated neoplastic conditions such as acute lymphoblastic leukemia, acute myeloblastic leukemia, Wilms' tumor, neuroblastoma, soft tissue and bone sarcomas, breast carcinoma, ovarian carcinoma, transitional cell bladder carcinoma, thyroid carcinoma, gastric carcinoma, Hodgkin's disease, malignant lymphoma and bronchogenic carcinoma in which the small cell histologic type is the most responsive compared to other cell types.

I am interested in presenting this molecule because it is a natural compound and successful in the treatment of cancer. However, there is still lots of development needed to cure cancer more effectively.

Refernce: https://pubchem.ncbi.nlm.nih.gov/compound/31703#section=Top