453565-59-8

Upstream product

• 69113-59-3 3-iodobenzonitrile 

Downstream Products

• 211943-47-4 3-(3-iodo-phenyl)-4H-[1,2,4]oxadiazol-5-one 
• 453567-10-7 3-(3-iodophenyl)-5-(pyridin-2-yl)-1,2,4-oxadiazole 
• 453567-11-8 3-(3-cyanophenyl)-5-(pyridin-2-yl)-1,2,4-oxadiazole 
• 180530-09-0 1-iodo-3-(5-methyl-[1,2,4]oxadiazol-3-yl)benzene 

Relevant academic research and scientific papers

Novel 5-(quinuclidin-3-ylmethyl)-1,2,4-oxadiazoles to investigate the activation of the α7 nicotinic acetylcholine receptor subtype: Synthesis and electrophysiological evaluation

α7 nicotinic acetylcholine receptors (nAChRs) are relevant therapeutic targets for a variety of disorders including neurodegeneration, cognitive impairment, and inflammation. Although traditionally identified as an ionotropic receptor, the α7 subtype showed metabotropic-like functions, mainly linked to the modulation of immune responses. In the present work, we investigated the structure-activity relationships in a set of novel α7 ligands incorporating the 5-(quinuclidin-3-ylmethyl)-1,2,4-oxadiazole scaffold, i.e. derivatives 21a-34a and 21b-34b, aiming to identify the structural requirements able to preferentially trigger one of the two activation modes of this receptor subtype. The new compounds were characterized as partial and silent α7 nAChR agonists in electrophysiological assays, which allowed to assess the contribution of the different groups towards the final pharmacological profile. Overall, modifications of the selected structural backbone mainly afforded partial agonists, among them tertiary bases 27a-33a, whereas additional hydrogen-bond acceptor groups in permanently charged ligands, such as 29b and 31b, favored a silent desensitizing profile at the α7 nAChR.

PYRIMIDODIAZEPINONE DERIVATIVE

The invention provides a pyrimidodiazepinone derivative represented by the general formula (I) [wherein n represents 1 or 2, Z represents a hydrogen atom or the like, R1 and R2 may be the same or different, and each represents a hydrogen atom or the like, A represents a bond, (CH2)m (wherein m represents an integer of 1 to 4), optionally substituted phenylene, optionally substituted pyridinediyl, or C=O, R3 represents a hydrogen atom, optionally substituted lower alkyl, or the like, and R4 represents a hydrogen atom or the like], or a pharmaceutically acceptable salt thereof or the like.

Novel non-carboxylic acid retinoids: 1,2,4-Oxadiazol-5-one derivatives

We have successfully obtained 1,2,4-oxadiazol-5-one bioisoteres of Am580 or Tazarotene-like retinoids. In particular compound 4 displays an EC50 of 26 nM on RAR-β.

A versatile solid-phase synthesis of 3-aryl-1,2,4-oxadiazolones and analogues

We report here the first method to load acidic heterocyclic compounds (1,2,4-oxadiazol-5-one, 1,2,4-oxadiazol-5-thione and 1,2,3,5-oxathiadazol-2-oxide) on a polymer. Using Mitsunobu conditions, these heterocycles were anchored on a 4-hydroxymethyl-3-methoxyphenoxybutyric acid benzhydrylamine (HMPB-BHA) resin. After diversification, compounds can be recovered by a simple treatment in diluted TFA. To illustrate the utility of this procedure, iodophenyl derivatives were anchored on the same resin. A HRMAS-NMR analysis shed light on the reactivity of these heterocycles in Mitsunobu conditions. A subsequent diversification using a Sonogashira coupling produced a small array of novel (arylethynyl)-phenyl-1,2,4-oxadiazol-5-ones.

Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists

The present invention provides compounds and pharmaceutical compositions that act as antagonists at metabotropic glutamate receptors, and that are useful for treating neurological diseases and disorders. Methods of preparing the compounds also are disclosed.