36626-24-1

Upstream product

• 117-80-6 2,3-Dichloro-1,4-naphthoquinone 
• 108-95-2 phenol 
• 83809-76-1 1-(4-hydroxyphenyl)-5-methyldihydrouracil 
• 1310679-87-8 1-[4-(3-chloro-1,4-dihydro-1,4-dioxonaphthalen-2-yloxy)-phenyl]-5,6-dihydro-5-methylpyrimidine-2,4(1H,3H)-dione 
• 90-15-3 α-naphthol 
• 130-15-4 [1,4]naphthoquinone 
• 139-02-6 sodium phenoxide 
• 100-67-4 potassium phenolate 

Downstream Products

• 101605-36-1 2-aziridin-1-yl-3-phenoxy-[1,4]naphthoquinone 
• 1301627-07-5 N-(3-phenoxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide 
• 102632-13-3 C₃₆H₂₄O₆ 
• 102632-12-2 2,2-Dimethyl-propionic acid 4-(2,2-dimethyl-propionyloxy)-2,3-diphenoxy-naphthalen-1-yl ester 
• 102632-11-1 Propionic acid 2,3-diphenoxy-4-propionyloxy-naphthalen-1-yl ester 
• 102632-10-0 2,3-diphenoxy-1,4-di(methylcarbonyloxy)naphthalene 

Relevant academic research and scientific papers

Structure-activity relationships and colorimetric properties of specific probes for the putative cancer biomarker human arylamine N-acetyltransferase 1

A naphthoquinone inhibitor of human arylamine N-acetyltransferase 1 (hNAT1), a potential cancer biomarker and therapeutic target, has been reported which undergoes a distinctive concomitant color change from red to blue upon binding to the enzyme. Here we describe the use of in silico modeling alongside structure-activity relationship studies to advance the hit compound towards a potential probe to quantify hNAT1 levels in tissues. Derivatives with both a fifty-fold higher potency against hNAT1 and a two-fold greater absorption coefficient compared to the initial hit have been synthesized; these compounds retain specificity for hNAT1 and its murine homologue mNat2 over the isoenzyme hNAT2. A relationship between pKa, inhibitor potency and colorimetric properties has also been uncovered. The high potency of representative examples against hNAT1 in ZR-75-1 cell extracts also paves the way for the development of inhibitors with improved intrinsic sensitivity which could enable detection of hNAT1 in tissue samples and potentially act as tools for elucidating the unknown role hNAT1 plays in ER+ breast cancer; this could in turn lead to a therapeutic use for such inhibitors.

1,4-QUINONES AND THEIR SULFUR ANALOGUES USEFUL AS LIGANDS OF N-ACETYLTRANSFERASES

The invention provides 1,4-quinones, 1,4-naphthoquinones and their sulphur analogues as inhibitors of hNAT1, an enzyme which is both a diagnostic marker and drug target for breast cancer. Some of the compounds of the invention are also chromogenic in the

Synthesis, chemical properties, and antimicrobial activity of 2- and 2,3-substituted [(tetrahydro-2,4-dioxopyrimidin-1(2H)-yl)phenoxy]naphthalene-1, 4-diones

Mono- and disubstituted [(tetrahydro-2,4-dioxopyrimidin-1(2H)-yl)phenoxy] naphthalene-1,4-diones were synthesized by the reaction of dihydro-1-(3-hydroxy- and 4-hydroxyphenyl)pyrimidine-2,4(1H,3H)-diones and their 5- and 6-methyl derivatives with 2,3-dichloro-1,4-naphthoquinone. Their stability in alkaline and acidic media was investigated. Four of the compounds exhibited good antimicrobial activity against Staphylococcus aureus, Mycobacterium luteum, Candida tenuis, and Aspergillus niger. Graphical abstract: [Figure not available: see fulltext.]

Water-promoted unprecedented chemoselective nucleophilic substitution reactions of 1,4-quinones with oxygen nucleophiles in aqueous micelles

Unique nucleophilic substitution and addition reactions of nitrogen and sulfur nucleophiles with 1,4-quinones in aqueous suspension with amines and thiols have recently been demonstrated by us.2 However, the reactivity of oxygen nucleophiles toward nucleophilic substitution compared to nitrogen and sulfur nucleophiles 'on water' is not facile. An unprecedented economical, green methodology approach using ordinary laundry detergent (LD; washing powder, 0.5 mol %, reusable)/SDS as surfactant 'in water' for nucleophilic substitution by oxygen nucleophiles in 1,4-quinones in excellent yields has been demonstrated.

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 anti-psoriatic agents

Psoriasis in mammals is relieved by topically administering naphthalenes of the formula: STR1 wherein: R1 and R2 are the same and are lower alkoxy or optionally substituted phenoxy, R3 is lower alkyl, lower alkoxy, or halo

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.

Naphthalene anti-psoriatic agents

Psoriasis in mammals is relieved by topically administering naphthalenes of the formula: STR1 wherein: R1 and R2 are the same and are lower alkoxy, lower alkylthio, optionally substituted phenoxy or optionally substituted phenylthio,