74237-20-0

Usage

InChI:InChI=1/C10H5ClO4/c11-4-1-2-5-6(3-4)8(13)10(15)9(14)7(5)12/h1-3,12-13H

Upstream product

• 124175-57-1 6-chloro-2,3-di-tert-butoxy-1,4-naphthoquinone 
• 102631-97-0 6-chloro-1,4-naphthoquinone 2,3-oxide 
• 56961-92-3 6-chloro-1,4-naphthoquinone 
• 106-51-4 p-benzoquinone 
• 14774-78-8 4-chlorophenyl lithium 
• 124175-56-0 4-(4-chlorophenyl)-2,3-di-tert-butoxy-4-hydroxycyclobut-2-en-1-one 
• 74237-21-1 6-chloro-2-hydroxynaphthalene-1,4-dione 

Relevant academic research and scientific papers

Synthesis of Hydroxyquinones and Related Compounds: Semisquaric Acids, (+/-)-Terreic Acid, (+/-)-Perezone, and (+/-)-Isoperezone

tert-Butoxyquinones were prepared from the thermal ring expansion of 4-alkynyl-, 4-alkenyl-, and 4-aryl-tert-butoxycyclobutenones and shown to be readily converted to hydroxyquinones upon treatment with trifluoroacetic acid at low temperature.This is a useful transformation since no reliable general route to hydroxyquinones has previously been available.The synthetic scope of this methodology as well as its specific utilization in the synthesis of a semisquaric acid, and the natural products, (+/-)-terreic acid, (+/-)-perezone, and (+/-)-isoperezone, are described.

Topical Nonsteroidal Antipsoriatic Agents. 1. 1,2,3,4-Tetraoxygenated Naphthalene Derivatives

On the basis of previous observations that both 2,3-dihydro-2,2,3,3-tetrahydroxy-1,4-naphthoquinone (oxoline, 1) and 6-chloroisonaphthazarin (2) had demonstrated antipsoriatic activity in vivo, a series of structural derivatives of 2 were prepared and examined in the Scholtz-Dumas topical psoriasis bioassay.Of these six (5, 6, 9a, 10, 11a, 11b), the most effective compound was found to be 6-chloro-1,4-diacetoxy-2,3-dimethoxynaphthalene (RS-43179,lonapalene, 11a).An extensive series of 1,2,3,4-tetraoxygenated naphthalenes (16-74) incorporating variations of the ester, eth er and aryl substituents were prepared as analogues of 11a to examine the structural requirements for activity and were screened in vivo as inhibitors of arachidonic acid induced mouse ear edema, a topical bioassay capable of detecting 5-lipoxygenase inhibitors.Net lipophilicity, hydrolytic stability, and ring substitution play significant roles in determining the observed in vivo activity.Lonapalene (11a) is currently in clinical development as a topical applied nonsteroidal antipsoriatic agent.

Naphthoquinone anti-psoriatic agents

Psoriasis in mammals is relieved by topically administering substituted naphthoquinone of the formula: STR1 wherein: R3 is halo, linear or branched alkoxy of one to eighteen carbon atoms or --S(O)n R wherein: n is 0, 1 or 2; and R is

Naphthoquinone anti-psoriatic agents

The 2,3-diesters of 6-substituted-2,3-dihydroxy-1,4-naphthoquinones exhibit useful anti-psoriatic activity in mammals.

Naphthaquinone anti-psoriatic agents

Psoriasis in mammals is relieved by topically administering substituted naphthaquinones of the formula: STR1 where R1 and R2 are the same or different and are hydrogen, hydroxy, alkoxy or acylamino and R3 is hydrogen, halo