25007-57-2

Upstream product

• 1010-60-2 2-chloro-1,4-naphthoquinone 
• 100-63-0 phenylhydrazine 

Relevant academic research and scientific papers

Aryl-free radical-mediated oxidative arylation of naphthoquinones using o-iodoxybenzoic acid and phenylhydrazines and its application toward the synthesis of benzocarbazoledione

Oxidative arylation of naphthoquinones has been developed through combination of o-iodoxybenzoic acid with arylhydrazines under mild conditions at open atmosphere. Arylated naphthoquinones with different electronic properties were obtained in moderate to good yields. The postulated radical mediated mechanism is supported by radical trapping experiments. Developed protocol for direct arylation of naphthoquinones has been extended toward short, high yielding, and an effective synthesis of antitumor-antibiotic precursor such as benzocarbazoledione.

Naphthalene anti-psoriatic agents

Psoriasis in mammals is relieved by topically administering naphthalenes of the formula: STR1 wherein: R1 is lower alkoxy or optionally substituted phenoxy; R2 is hydrogen, lower alkyl, optionally substituted phenyl or optionally substituted phenyl-lower-alkyl; R3 is hydrogen, lower alkyl, lower alkoxy, halo, optionally substituted phenyl, optionally substituted phenyl-lower-alkyl or optionally substituted phenyl-lower-alkoxy, and m is 1 or 2; X and Y are different and are selected from the group consisting of hydrogen, R4 and -C(O)W, wherein W is alkyl of one to seven carbon atoms, optionally substituted phenyl or optionally substituted benzyl; and R4 is lower alkyl or optionally substituted phenyl-lower-alkyl.

Naphthalene anti-psoriatic agents

Psoriasis in mammals is relieved by topically administering naphthalenes of the formula: STR1 wherein: R1 is alkoxy, alkylthio, optionally substituted phenoxy or optionally substituted phenylthio; R2 is hydrogen, lower alkyl, optionally substituted phenyl or optionally substituted phenylalkyl; R3 is lower alkyl, lower alkoxy, or halo and m is 0, 1 or 2, or R3 is optionally substituted phenyl, optionally substituted phenyl lower alkyl, optionally substituted phenyl lower alkoxy, amino, lower alkylamino, lower dialkylamino, cyano, or S(0)n R wherein R is lower alkyl; optionally substituted phenyl; optionally substituted phenyl lower alkyl; or optionally substituted heterocyclic aryl of three to nine ring atoms containing one or two heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and the pharmaceutically acceptable acid addition salts thereof; and m is 1 and n is 0, 1 or 2; and W is alkyl of one to seven carbon atoms, optionally substituted phenyl or optionally substituted benzyl.

METHOD FOR TREATING DISEASE STATES IN MAMMALS WITH NAPHTHALENE LIPOXYGENASE-INHIBITTNG AGENTS

Psoriasis in mammals is relieved by topically administering naphthalenes of the formula: wherein: R1 is lower alkoxy or optionally substituted phenoxy, R2 is the same as R1, or R2 is hydrogen, lower alkyl, optionally substituted phenyl or optionally substituted phenylalkyl, R3 is hydrogen, lower alkyl, lower alkoxy, halo, optionally substituted phenyl, optionally substituted phenyl-lower-alkyl or optionally substituted phenyl-lower-alkoxy, and m is 1 or 2; both X groups are the same and X is either -C(O)OR4 or -C(O)NR5R6 , wherein R4 is alkyl, phenyl or benzyl optionally substituted with one or two lower alkyl groups, lower alkoxy groups or halo; and R5 and R6 are independently hydrogen, lower alkyl, cycloalkyl or phenyl optionally substituted with one or two lower alkyl groups, lower alkoxy groups or halo. The compounds of this invention are also useful for the treatment of disease-states caused by lipoxygenase activity in mammals, particularly 5-lipoxygenase activity, when administered systemically.

Naphthalene lipoxygenase-inhibiting agents

Psoriasis in mammals is relieved by topically administering naphthalenes of the formula: STR1 wherein: R1 is lower alkoxy or optionally substituted phenoxy; R2 is hydrogen, lower alkyl, optionally substituted phenyl or optionally substituted phenylalkyl; R3 is hydrogen, lower alkyl, lower alkoxy, halo, optionally substituted phenyl, optionally substituted phenyl-lower-alkyl or optionally substituted phenyl-lower-alkoxy, and m is 1 or 2; X and Y are different and are either R4 or --C(O)W wherein R4 is lower alkyl or optionally substituted phenyl-lower-alkyl; W is --OR5 or --NR6 R7, wherein R5 is alkyl, optionally substituted phenyl or optionally substituted benzyl; and R6 and R7 are independently hydrogen, lower alkyl, cycloalkyl or optionally substituted phenyl. The compounds of this invention are also useful for the treatment of disease-states caused by lipoxygenase activity in mammals, particularly 5-lipoxygenase activity, when administered systemically.

Naphthalene anti-psoriatic agents

Psoriasis in mammals is relieved by topically administering naphthalenes of the formula: STR1 wherein: R1 is lower alkoxy or optionally substituted phenoxy; R2 is hydrogen, lower alkyl, optionally substituted phenyl or optionally substituted phenylalkyl; R3 is hydrogen, lower alkyl, lower alkoxy, halo, optionally substituted phenyl, optionally substituted phenyl-lower-alkyl or optionally substituted phenyl-lower-alkoxy, and m is 1 or 2; X and Y are different and are either R4 or --C(O)W wherein R4 is lower alkyl or optionally substituted phenyl-lower-alkyl; W is --OR5 or --NR6 R7, wherein R5 is alkyl, optionally substituted phenyl or optionally substituted benzyl; and R6 and R7 are independently hydrogen, lower alkyl, cycloalkyl or optionally substituted phenyl.

Method for the hydrocarbylation of naphthoquinone derivatives

A method for the hydrocarbylation of naphthoquinones comprising cross-coupling addition of the hydrocarbyl moiety of selected organometallic reagents to leaving group-substituted naphthoquinones.