1215-99-2Relevant articles and documents
Synthesis of novel 1,2,4-trioxanes and antimalarial evaluation against multidrug-resistant Plasmodium yoelii nigeriensis
Hassam, Mohammad,Kumar Yadav, Dinesh,Prakash Verma, Ved,Puri, Sunil K.,Sharma, Siddharth,Shrivastava, Rahul,Shukla, Monika,Singh, Chandan
, (2021/08/21)
Malaria epidemics represent one of the life-threatening diseases to low-income lying countries which subsequently affect the economic and social condition of mankind. In continuation in the development of a novel series of 1,2,4-trioxanes 13a1-c1, 13a2-c2, and 13a3-c3 have been prepared and further converted into their hemisuccinate derivatives 14a1-c1, 14a2-c2, and 14a3-c3 respectively. All these new compounds were evaluated for their antimalarial activity against multidrug-resistant Plasmodium yoelii nigeriensis in mice by both oral and intramuscular (im) routes. Hydroxy-functionalized trioxane 13a1 showed 80% protection and its hemisuccinate derivative 14a1 showed 100% protection at a dose of 48 mg/kg × 4 days by both routes, which is twice active than artemisinin by oral route.
COMPOUND
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Page/Page column 143-144, (2008/06/13)
There is provided a compound of Formula (I):wherein R3, R4, R5, R6, R7, R9, and R10, are independently selected from -H, -OH, hydrocarbyl groups, oxyhydrocarbyl groups, cyano (-CN), nitro (-NO2 ), and halogens; wherein ring A is optionally further substituted wherein X is a bond or a linker group wherein (A) (i) R9 is selected from alkyl and halogen groups; and (ii) R10 is selected from -OH, oxyhydrocarbyl and -OSO 2 NR1 R2 ; wherein R1 and R2 are independently selected from H and hydrocarbyl or (B) at least one of R3 , R4 , R5 , R6 and R7 is the group -C(=0)-CR11 R12 -R8 wherein R8 is a selected from (i) an alkyloxyalkyl group (ii) a nitrile group, (iii) alkylaryl group, wherein the aryl group is substituted by other than a C1-10 group (iv) alkenylaryl group wherein the aryl group is substituted (v) alkylheteroaryl group, wherein when heteroaryl group comprises only C and N in the ring, the aryl group is substituted by other than a methyl group (vi) alkenylheteroaryl group (vii) =N-O-alkyl or =N-O-H group (viii) branched alkenyl (ix) alkyl-alcohol group or alkenyl-alcohol group (x) amide or alkylamide wherein (a) the alkyl of the alkylamide is -CH 2 - or - CH 2 CH 2 -, (b) the amide is di-substituted and/or (c) the amide is substituted with at least one of alkylheterocycle group, alkenylheterocycle group, alkylheteroaryl group, alkenylheteroaryl group, heteroaryl group, alkylamine group, alkyloxyalkyl group, alkylaryl group, straight or branched alkyl group, (xi)-CHO, or together with another of R3 , R4 , R5 , R6 and R7 the enol tautomer thereof wherein R11 and R12 are independently selected from H and hydrocarbyl; or (C) at least one of R3 , R4 , R5 , R6 and R7 together with another of R3 , R4 , R5 , R6 and R7 forms a ring containing -C(=O)-; or (D) at least one of R3 , R4 , R5 , R6 and R7 is selected from alkylheterocycle group, alkenylheterocycle group, alkylheteroaryl group, alkenylheteroaryl group, and heteroaryl groups or (E) at least one of R3 , R4 , R5 , R6 and R7 is selected from -CN, -C(R13 )=N-O-alkyl group, - C(R14 )=N-O-H group, optionally substituted pyrazole, optionally substituted thiazole, optionally substituted oxazole, optionally substituted isoxazole, optionally substituted pyridine, and optionally substituted pyrimidine, or together with another of R3 , R4 , R5 , R6 and R7 forms a nitrogen containing ring; wherein R13 and R14 are independently selected from H and hydrocarbyl
Cyclodienones. X. Reaction of Halo-cyclohexadien-1-ones with Phenols in the Presence of α-Picoline and Preparation of 4-Hydroxy- and 2-Hydroxyphenyl Aryl Ethers
Tashiro, Masashi,Itoh, Takashi,Fukata, Gouki
, p. 416 - 420 (2007/10/02)
Reaction of 4-halocyclohexadienones such as 4-bromo-(1a), 4-chloro-2,4,6-tri-t-butyl-(1b), 2,4-dichloro-4,6-di-t-butyl-2,5-cyclohexadien-1-one, and 2,4-dichloro-2,6-di-t-butyl-3,5-cyclohexadien-1-one with phenols in the presence of α-picoline was carried out under various conditions.The reaction of 1a and 1b with phenols afforded the corresponding 2-aryloxy-4,6-di-t-butyl phenols together with various by-products.The AlCl3 catalyzed trans-t-butylation of 2-aroxy-4,6-di-t-butyl-phenols, which were obtained by the above reaction, afforded the corresponding 2-hydroxyphenyl aryl ethers.The similar reaction of 4-aroxy-2,4,6-tri-t-butyl-2,5-cyclohexadien-1-ones also afforded the corresponding 4-hydroxyphenyl aryl ethers.