Provided herein are naphthoquinones compounds such as those with a hydrogen bond donating group of the formula (I): wherein: R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, and n are as defined herein. Also provided herein are pharmaceutical composition of the present compounds and methods of treatment using the compounds including their use in the treatment of cancer.

##STR00001##

Provided herein are naphthoquinones compounds such as those with a hydrogen bond donating group of the formula (I): wherein: R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, and n are as defined herein. Also provided herein are pharmaceutical composition of the present compounds and methods of treatment using the compounds including their use in the treatment of cancer.

##STR00001##

In a production method of the present disclosure, a 1,1-binaphthyl precursor derivative, an organic acid, and an iodinating or brominating agent are mixed. The 1,1-binaphthyl precursor derivative has a 1,1-binaphthyl skeleton and has an electron-donating group at the 2-position of the 1,1-binaphthyl skeleton and at the 2-position of the 1,1-binaphthyl skeleton, and the electron-donating group contains an oxygen atom directly bonded to the skeleton. With the production method of the present disclosure, a 1,1-binaphthyl derivative having a substituent introduced at the 8-position and/or 8-position of the 1,1-binaphthyl skeleton can be obtained. The 1,1-binaphthyl derivative obtained by the production method of the present disclosure can be a compound further having a substituent introduced at at least one position selected from the 4-position, 4-position, 5-position, 5-position, 6-position, and 6-position of the 1,1-binaphthyl skeleton.

In a production method of the present disclosure, a 1,1-binaphthyl precursor derivative, an organic acid, and an iodinating or brominating agent are mixed. The 1,1-binaphthyl precursor derivative has a 1,1-binaphthyl skeleton and has an electron-donating group at the 2-position of the 1,1-binaphthyl skeleton and at the 2-position of the 1,1-binaphthyl skeleton, and the electron-donating group contains an oxygen atom directly bonded to the skeleton. With the production method of the present disclosure, a 1,1-binaphthyl derivative having a substituent introduced at the 8-position and/or 8-position of the 1,1-binaphthyl skeleton can be obtained. The 1,1-binaphthyl derivative obtained by the production method of the present disclosure can be a compound further having a substituent introduced at at least one position selected from the 4-position, 4-position, 5-position, 5-position, 6-position, and 6-position of the 1,1-binaphthyl skeleton.

Disclosed herein are 1,4-naphthoquinone analogs, pharmaceutical compositions that include one or more of such 1,4-naphthoquinone analogs, and methods of treating and/or ameliorating diseases and/or conditions associated with a cancer, such as prostate cancer with such 1,4-naphthoquinone analogs. Also included are combination therapies wherein a 1,4-naphthoquinone analog disclosed herein, and a hormone therapy agent are provided to a subject suffering from a condition such as cancer.

Disclosed herein are 1,4-naphthoquinone analogs, pharmaceutical compositions that include one or more of such 1,4-naphthoquinone analogs, and methods of treating and/or ameliorating diseases and/or conditions associated with a cancer, such as prostate cancer with such 1,4-naphthoquinone analogs. Also included are combination therapies wherein a 1,4-naphthoquinone analog disclosed herein, and a hormone therapy agent are provided to a subject suffering from a condition such as cancer.

Provided is a method of producing 2-hydroxy-1,4-naphthoquinone in a large amount, a high yield, and inexpensively. This method comprises oxidizing 2-hydroxynaphthalene with hydrogen peroxide in (1) an alkaline aqueous solution or in (2) a mixture of an alkaline aqueous solution with an inert organic solvent incompatible with water, in the presence of a vanadium catalyst.

Provided is a method of producing 2-hydroxy-1,4-naphthoquinone in a large amount, a high yield, and inexpensively. This method comprises oxidizing 2-hydroxynaphthalene with hydrogen peroxide in (1) an alkaline aqueous solution or in (2) a mixture of an alkaline aqueous solution with an inert organic solvent incompatible with water, in the presence of a vanadium catalyst.

Described herein are compounds of Formula I: ##STR00001##
wherein R.sub.1-R.sub.6 are as described herein, for use in the treatment of a coronavirus infection; a method of inhibiting a coronavirus 3CL protease, by contacting the 3CL protease with a compound of Formula I; as well as methods pharmaceutical composition comprising a compound of Formula I and at least one phospholipid, wherein a weight ratio of the phospholipid(s) to the compound in the composition is in a range of from 10:1 to 1:10. Further described herein is a method of treating a coronavirus infection in a subject in need thereof, by administering to the subject at least one compound that exhibits at least two of: inhibition of an activity of a 3CL protease of the coronavirus; inhibition of inflammation in the subject; and inhibition of autophagy in the subject.

The present application provides vitamin K metabolite derivatives and methods for preparing vitamin K metabolites and metabolite derivatives.