Enaminone-grafted trithiocarbonate with anticancer and antimicrobial activity

Patent metadata

Field	Value
Publication number	US-10071960-B1
Application number	US-201715726263-A
Country	US
Kind code	B1
Filing date	Oct 5, 2017
Priority date	Oct 5, 2017
Publication date	Sep 11, 2018
Grant date	Sep 11, 2018

Abstract

The present subject matter is directed to an enaminone-grafted trithiocarbonate compound having the structure:

and the anticancer and antimicrobial activities exhibited by the compound.

First claim

We claim:

1. A compound having the formula:

or a pharmaceutically acceptable salt thereof.

2. A pharmaceutical composition, comprising the compound according to claim 1 and a pharmaceutically acceptable carrier.

3. A method of treating a disease, comprising:
administering to a patient a therapeutically effective amount of the pharmaceutical composition according to claim 2 , wherein the disease is cancer and the cancer is selected from the group consisting of liver cancer, colon cancer, and breast cancer or the disease is a fungal infection.

4. The method of claim 3 , wherein the fungal infection is caused by a yeast or mold.

5. The method of claim 4 , wherein the yeast or mold is Candida albicans.

6. The method of claim 4 , wherein the yeast or mold is Cryptococcus neoformans.

7. The method of claim 4 , where the yeast or mold is Aspergillus fumigatus.

8. The method of claim 4 , where the yeast or mold is Penicillium chrysogenum.

9. The method of claim 3 , wherein the disease fungal infection is caused by a bacteria.

10. The method of claim 9 , wherein the bacteria is Streptococcus mutans.

11. The method of claim 9 , wherein the bacteria is Salmonella typhi.

12. A method of synthesizing a compound, comprising:
mixing diethyl 2,2′-(thiocarbonylbis(sulfanediyl))diacetate with N,N′-dimethylformamide dimethyl acetal to form a mixture; and
heating the mixture to at least about 100° C. for at least about one hour to form a heated mixture including the compound having the structure:

13. The method of claim 12 , further comprising:
allowing the heated mixture to cool to room temperature to form a cooled mixture;
maintaining the cooled mixture for at least about 8-10 hours to form a maintained mixture; and
isolating the compound from the maintained mixture.

14. The method of claim 13 , wherein the compound is in crystal form.

15. The method of claim 12 , further comprising a preliminary step of reacting ethyl cyanoacetate, carbon disulfide (CS2), and ethyl 2-chloroacetate to synthesize the diethyl 2,2′-(thiocarbonylbis(sulfanediyl))diacetate.

Assignees

• Univ King Saud

Inventors

• Mabkhot Yahia Nasser
• Khaled Jamal Mohammed Ali
• Sultan Mujeeb Abdullah
• Mohammed Fahd Ali Nasr
• Alharbi Naiyf Sultan Helial Alaloi
• Al-Showiman Salim Showiman
• Ghabbour Hazem Ahmed

Classifications

• C07C329/06 Primary

  having sulfur atoms of thiocarbonic groups bound to acyclic carbon atoms · CPC title

• C07C329/00 Primary

  Thiocarbonic acids; Halides, esters or anhydrides thereof · CPC title