178876-99-8

Upstream product

• 3132-99-8 m-bromobenzoic aldehyde 
• 144-55-8 sodium hydrogencarbonate 
• 123-25-1 succinic acid diethyl ester 
• 178877-00-4 4-Acetoxy-7-bromo-naphthalene-2-carboxylic acid ethyl ester 

Downstream Products

• 178877-03-7 ethyl 4-Benzyloxy-7-bromo-2-naphthalenecarboxylate 
• 1160269-99-7 ethyl 7-(4-(trifluoromethyl)phenyl)-4-hydroxy-2-naphthoate 
• 1160270-28-9 ethyl 4-hydroxy-7-[4-(methylthio)phenyl]-2-naphthoate 
• 1160270-65-4 ethyl 7-bromo-3-fluoro-4-hydroxy-2-naphthoate 
• 1160271-34-0 tert-butyl 4-(4-(3-(ethoxycarbonyl)-6-(4-(trifluoromethyl)phenyl)naphthalen-1-yl)phenyl)piperidine-1-carboxylate 
• 1160271-35-1 4-(4-(1-(tert-butoxycarbonyl)piperidin-4-yl)phenyl)-7-(4-(trifluoromethyl)phenyl)-2-naphthoic acid 
• 1160271-30-6 4-[4-(4-piperidinyl)phenyl]-7-[4-(trifluoromethyl)phenyl]-2-naphthalenecarboxylic acid 
• 1021906-41-1 ethyl 8-bromo-2-phenyl-2-(4-piperidinophenyl)-2H-naphtho[1,2-b]pyran-5-carboxylate 
• 1160270-44-9 C₂₀H₁₅F₃O₄ 
• 1325731-14-3 C₂₆H₂₉BO₅ 
• 1160270-14-3 ethyl 7-(4-(trifluoromethyl)phenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-naphthoate 
• 1325731-55-2 C₂₆H₂₆BF₃O₅ 
• 1160270-01-8 ethyl 7-(4-(trifluoromethyl)phenyl)-4-(((trifluoromethyl)sulfonyl)oxy)-2-naphthoate 
• 1160270-46-1 ethyl 7-[4-(trifluoromethoxy)phenyl]-4-{[(trifluoromethyl)sulfonyl]oxy}-2-naphthoate 

Relevant academic research and scientific papers

PHOTO RESPONSIVE MATERIAL AND OPTICAL DEVICE

An optical device is provided, which includes a first transparent substrate, a second transparent substrate, and a liquid-crystal material disposed between the first transparent substrate and the second transparent substrate. The liquid-crystal material includes a photo responsive material with a chemical structure of: wherein A1 is A2 and A3 are independently X is halogen. R is H, C1-12 alkyl group, or C1-12 alkoxy group. R′ is C1-12 alkyl group.

CYCLIC PRODRUGS OF DUOCARMYCIN ANALOGS

The invention provides prodrugs of DNA-reactive analogs of duocarmycin and CC-1065 anticancer agents, wherein a cyclic prodrug form, such as carbamate, thionocarbamate, or carbamimidate, can be hydrolyzed by the patient in vivo to yield a respective bioac

Analogs of CC-1065 and the duocarmycins

PCT No. PCT/US97/09076 Sec. 371 Date Sep. 7, 1999 Sec. 102(e) Date Sep. 7, 1999 PCT Filed May 30, 1997 PCT Pub. No. WO97/45411 PCT Pub. Date Dec. 4, 1997Analogs of antitumor antibiotics CC-1065 and the duocarmycins are synthesized which possess systematic

Synthesis, chemical properties, and preliminary evaluation of substituted CBI analogs of CC-1065 and the duocarmycins incorporating the 7-cyano-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one alkylation subunit: Hammett quantitation of the magnitude of electronic effects on functional reactivity

The synthesis of 7-cyano-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one (CCBI), a substituted CBI derivative bearing a C7 cyano group, is described in efforts that establish the magnitude of potential electronic effects on the functional reactivity of the agents. The CCBI alkylation subunit was prepared by a modified Stobbe condensation/Friedel-Crafts acylation for generation of the appropriately functionalized naphthalene precursors followed by 5-exo-trig aryl radical-alkene cyclization for synthesis of the 1,2-dihydro-3H-benz[e]indole skeleton and final Ar-3′ alkylation for introduction of the activated cyclopropane. The most concise approach provided the CCBI subunit and its immediate precursor in 14-15 steps in superb overall conversions (15-20percent). Resolution of an immediate CCBI precursor and its incorporation into both enantiomers of 34-39, analogs of CC-1065 and the duocarmycins, are detailed. A study of the solvolysis reactivity and regioselectivity of N-BOC-CCBI (25) revealed that introduction of the C7 nitrile slowed the rate of solvolysis but only to a surprisingly small extent. Classical Hammett quantitation of the effect provided a remarkably small ρ (-0.3), indicating an exceptionally small C7 substituent electronic effect on functional reactivity. Additional kinetic studies of acid-catalyzed nucleophilic addition proved inconsistent with C4 carbonyl protonation as the slow and rate-determining step but consistent with a mechanism in which protonation is rapid and reversible followed by slow and rate-determining nucleophilic addition to the cyclopropane requiring both the presence and assistance of a nucleophile (SN2 mechanism). No doubt this contributes to the DNA alkylation selectivity of this class of agents and suggests that the positioning of an accessible nucleophile (adenine N3) and not C4 carbonyl protonation is the rate-determining step controlling the sequence selectivity of the DNA alkylation reaction. This small electronic effect on the solvolysis rate had no impact on the solvolysis regioselectivity, and stereoelectronically-controlled nucleophilic addition to the least substituted carbon of the activated cyclopropane was observed exclusively. Consistent with past studies, a direct relationship between solvolysis stability and cytotoxic potency was observed with the CCBI-derived agents providing the most potent analogs in the CBI series, and these observations were related to the predictable Hammett substituent effects. For the natural enantiomers, this unusually small electronic effect on functional reactivity had no perceptible effect on their DNA alkylation selectivity. Similar effects of the C7 cyano substituent on the unnatural enantiomers were observed, and they proved to be 4-10× more effective than the corresponding CBI-based unnatural enantiomers and 4-70× less potent than the CCBI natural enantiomers.