5395-25-5

Upstream product

• 3166-15-2 thioxanthen-9-one 10,10-dioxide 
• 492-22-8 thio-xanthene-9-one 

Relevant academic research and scientific papers

Relationship between structure of conjugated oxime esters and their ability to cleave DNA

The size and geometry of polycycles are critical to intercalation into DNA. This work involves the establishment of a new compound library that includes 35 O-benzoyl oxime esters with intercalators of five types. These conjugated compounds were synthesized by the condensation of substituted benzoyl chlorides (XC6H4COCl; X = H, Me, CN, F, and NO2) or naphthoyl chlorides with oximes of fluoren-9-one, 9,10-anthraquinone, xanthen-9-one, thioxanthen-9-one, and 9H-thioxanthen-9-one 10,10-dioxide to give the corresponding esters in 80-99% yields. All of these compounds could cleave DNA when photolyzed by UV light. Of these conjugates, 9,10-anthraquinone-O-9-(4- fluorobenzoyl)oxime with a binding constant of 4.49 × 104 M-1 cleaved DNA most efficiently. Examination of the structure-activity relationship supports a conclusion that two factors affect DNA-cleaving potency. These are (1) the planarity of the intercalating moiety, and (2) the size and substituents of the benzoyl ring. The DNA-cleaving ability followed the order 9,10-anthraquinone > fluoren-9-one ≥ xanthen-9-one ～ thioxanthen-9-one > 9H-thioxanthen-9-one 10,10-dioxide. The benzoyl-containing oxime ester conjugates were more active than the corresponding naphthoyl-containing conjugates. The potency that was associated with the different substituents on the benzoyl ring followed the order F > CN ≥ NO2 > Me ～ H.

Oxime esters of anthraquinone as photo-induced DNA-cleaving agents for single- and double-strand scissions

Anthraquinone-O-9-(4-cyanobenzoyl)oxime (13) with binding constant of 4.49×104 M-1 exhibited single-strand scission of DNA at the concentration of 10 μM and double-strand scission at 50 μM upon UV irradiation.

New approach to biomimetic transamination using bifunctional [1,3]-proton transfer catalysis in thioxanthenyl dioxide imines

A pyridoxamine equivalent, 9-aminothioxanthene 10,10-dioxide, has been designed that is capable of affording transamination in good to excellent yields of natural as well as artificial amino acids. Amidines and guanidines in catalytic amounts were capable of performing [1,3]-proton transfer in the imines under mild conditions, whereas various simple amines failed. The use of chiral catalysts resulted in modest asymmetric induction (ee ≤ 45%). The electronic dependence in para-substituted phenyl glyoxylate imines, isotope effects, and computational studies support a stepwise, bifunctional mechanism for amidine and guanidine catalysts. Attempts toward an autocatalytic model system are described.

On the Synthesis of 3-Amino-2,3-dihydro-1H-pyridophenothiazine 5,5-Dioxide and of 3-Amino-1,2-dihydro-3H-dibenzopyrido-1,4-thiazepine 7,7-Dioxide

3-Amino-2,3-dihydro-1H-pyridophenothiazine 5,5-dioxide and 3-amino-1,2-dihydro-3H-dibenzopyrido-1,4-thiazepine 7,7-dioxide were synthesized from the corresponding 3-oxime acetates by reduction with the borane-tetrahydrofuran complex.Reduction was not successful in the case of 2,3-dihydro-1H-pyridophenothiazine-3-oxime acetate.