109249-04-9Relevant academic research and scientific papers
Total synthesis of thiaplakortone A: Derivatives as metabolically stable leads for the treatment of malaria
Pouwer, Rebecca H.,Deydier, Sophie M.,Le, Phuc Van,Schwartz, Brett D.,Franken, Nicole C.,Davis, Rohan A.,Coster, Mark J.,Charman, Susan A.,Edstein, Michael D.,Skinner-Adams, Tina S.,Andrews, Katherine T.,Jenkins, Ian D.,Quinn, Ronald J.
, p. 178 - 182 (2014)
Thiaplakortone A (3a), an antimalarial natural product, was prepared by an operationally simple and scalable synthesis. In our efforts to deliver a lead compound with improved potency, metabolic stability, and selectivity, the synthesis was diverted to access a series of analogues. Compounds 3a-d showed nanomolar activity against the chloroquine-sensitive (3D7) Plasmodium falciparum line and were more active against the chloroquine- and mefloquine-resistant (Dd2) P. falciparum line. All compounds are "Rule-of-5" compliant, and we show that metabolic stability can be enhanced via modification at either the primary or pyrrole nitrogen. These promising results lay the foundation for the development of this structurally unprecedented natural product.
NITRATED PSILOCYBIN DERIVATIVES AND USE THEREOF FOR MODULATING 5-HT2A RECEPTOR AND FOR TREATING A PSYCHIATRIC DISORDER
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Paragraph 00101, (2022/03/22)
Disclosed are nitrated psilocybin compounds of formula (I), wherein at least one of R2, R4, R5, R6, or R7, is a nitro group, and wherein each non-nitrated R2, R5, R6, or R7, is a hydrogen atom, an alkyl, O-alkyl or O-aryl group, wherein R4 when it is not nitrated is a hydrogen atom, an alkyl, O-alkyl or O-aryl group, a hydroxy group, or a phosphate group, and wherein R3a, and R3b, are a hydrogen atom, an alkyl group, an aryl group, or an acyl group, pharmaceutical formulations containing the same. The nitrated psilocybin compounds of formula (I) may be chemically synthesized or biochemically synthesized in host cells. The nitrated compounds of formula (I) may be used for modulating 5-HT2A receptor, and for treating a psychiatric disorder in a subject.
Synthetic studies of psilocin analogs having either a formyl group or bromine atom at the 5- or 7-position.
Yamada, Fumio,Tamura, Mayumi,Hasegawa, Atsuko,Somei, Masanori
, p. 92 - 99 (2007/10/03)
Psilocin analogs having either a formyl group (9-12) or a bromine atom (13-18) at the 5- or 7-position have been prepared for the first time. Syntheses of 5- and 7-bromo derivatives of 4-hydroxy- (23, 24, 28) and 4-benzyloxyindole-3-carbaldehyde (19, 25,
A five-step synthesis of psilocin from indole-3-carbaldehyde
Yamada, Fumio,Tamura, Mayumi,Somei, Masanori
, p. 451 - 457 (2007/10/03)
A novel preparative method of psilocin was established in only five steps from indole-3-carbaldehyde in 50% overall yield.
