Diversity oriented total synthesis (DOTS) of pyridoquinazolinone alkaloids and their analogues.

A short diversity oriented total synthesis (DOTS) of substituted rutaecarpines, homo-luotonins, homo-vasicinone, homo-isaindigotones and homo-vasnetine has been achieved from the key tricyclic intermediate. The [] tricyclic ketone, the mackinazolindione, was accessed from simple substrates quinazolinone diester obtained from the disubstituted anthranilamide which in turn was prepared from the coupling of amino acid ester and ethyl oxalyl chloride with isatoic anhydride and Dieckmann condensation chemistry.

Structure-Activity Relationships for Psilocybin, Baeocystin, Aeruginascin, and Related Analogues to Produce Pharmacological Effects in Mice.

4-Phosphoryloxy-,-dimethyltryptamine (psilocybin) is a naturally occurring tertiary amine found in many mushroom species. Psilocybin is a prodrug for 4-hydroxy-,-dimethyltryptamine (psilocin), which induces psychedelic effects via agonist activity at the serotonin (5-HT) 2A receptor (5-HT). Several other 4-position ring-substituted tryptamines are present in psilocybin-containing mushrooms, including the secondary amine 4-phosphoryloxy--methyltryptamine (baeocystin) and the quaternary ammonium 4-phosphoryloxy-,,-trimethyltryptamine (aeruginascin), but these compounds are not well studied.

A New Chemotype of Chemically Tractable Nonsteroidal Estrogens Based on a Thieno[2,3-]pyrimidine Core.

Despite continued interest in the development of nonsteroidal estrogens and antiestrogens, there are only a few chemotypes of estrogen receptor ligands. Using targeted screening in a ligand sensing assay, we identified a phenolic thieno[2,3-]pyrimidine with affinity for estrogen receptor α. An efficient three-step synthesis of the heterocyclic core and structure-guided optimization of the substituents resulted in a series of potent nonsteroidal estrogens.

'Foxtrot' fumarate: a water-soluble salt of ,-di-allyl-5-methoxytryptamine (5-MeO-DALT).

The title compound, bis-(,-diallyl-5-meth-oxy-tryptammonium) (5-MeO-DALT) fumarate (systematic name: bis-{-[2-(5-meth-oxy-1-indol-3-yl)eth-yl]- -(prop-2-en-1-yl)prop-2-en-1-aminium} ()-but-2-enedioate), 2CHNO·CHO , has a single tryptammonium cation and half of a fumarate dianion in the asymmetric unit. The tryptammonium and fumarate ions are held together in one-dimensional chains by a series of N-H⋯O hydrogen bonds. These chains are combinations of (22) rings, and (14) and (28) parallel chains along [111].

Influence of dityrosine nanotubes on the expression of dopamine and differentiation in neural cells.

In this study, we report the synthesis of self-assembled dityrosine nanotubes as a biologically functional scaffold and their interactions with neural cells. Quantum chemical methods were used to determine the forces involved in the self-assembly process. The physicochemical properties of the nanostructures relevant to their potential as bioactive scaffolds were characterized.

The hydro-chloride salt of 4-hy-droxy-,-di--propyl-tryptamine (4-HO-DPT).

The title compound, 4-hy-droxy-,-di--propyl-tryptammonium (4-HO-DPT) chloride {systematic name: -[2-(4-hy-droxy-1-indol-3-yl)eth-yl]--propyl-propan-1-aminium chloride}, CHNO·Cl, has a singly protonated trypt-ammonium cation and one chloride anion in the asymmetric unit. A series of N-H⋯Cl and O-H⋯Cl hydrogen bonds connect the ions together in ladder chains along [010].

Synthesis and biofilm inhibition studies of 2-(2-amino-6-arylpyrimidin-4-yl)quinazolin-4(3H)-ones.

Synthesis of novel 4(3H)-quinazolinonyl aminopyrimidine derivatives has been achieved via quinazolinonyl enones which in turn were obtained from 2-acyl-4(3H)-quinazolinone. They have been assayed for biofilm inhibition against Gram-positive (methicillin-resistant Staphylococcus aureus (MRSA)) and Gram-negative bacteria (Acinetobacter baumannii). The analogues with 2,4,6-trimethoxy phenyl, 4-methylthio phenyl, and 3-bromo phenyl substituents (5h, 5j & 5k) have been shown to inhibit biofilm formation efficiently in MRSA with IC values of 20.