Spirocyclic CompoundsDownload PDF
A spiro compound is a bicyclic organic compound with rings connected through just one atom. The rings can be different in nature or identical. The connecting atom, called the spiroatom, is most often a quaternary carbon ("spiro carbon").
The structural rigidity and feasibility for further structural elaboration through three-dimensional space have allowed spiro-bicyclic compounds to be applied in many bioactive molecules; this is one of the key strategies in modern medicinal chemistry.
J&K Scientific categorizes these novel spiro compounds based simply on their ring systems. For instance, 2-Oxa-6-azaspiro[3.4]octane is one of the chemicals of the 5+4 system.
■ [6+5]-Spirocyclic compounds:
2-Boc-2,8-Diaza-spiro[4.5]decane has been used as the key intermediate in the synthesis of spirofused piperazine and diazepane amides. These compounds should provide useful starting points and tools to investigate further the importance of selective H3 antagonists for drug therapy in a variety of potential disease states.
References J. Med. Chem., 2014, 57, 733?758
■ [6+6]-spirocyclic compounds:
3,9-diazaspiro[5.5]undecane has been used in the synthesis of the analogues of adhesamine. A study combined chemical, physicochemical, and cell biological experiments, using adhesamine and its analogues, to examine the mechanism by which this dumbbell-shaped, nonpeptidic molecule induces physiologically relevant cell adhesion. The results suggest that multiple adhesamine molecules cooperatively bind to heparan sulfate and induce its assembly, promoting clustering of heparan sulfate-bound syndecan-4 on the cell surface.
J. Am. Chem. Soc., 2013, 135, 11032?11039
|1574407||9-Benzyl-2,9-diazaspiro[5.5]undecane dihydrochloride, 95%||1198286-24-6||Pricing|
|536697||3-Boc-3,9-diazaspiro[5.5]undecane hemioxalate, 95%||173405-78-2||Pricing|
■ [6+4]-spirocyclic compounds:
Modified by an oxetane spiro-fused piperidine, the derivatives of YM-53403 have been found to give significantly improved antiviral activity against RSV A2 and RSV B-WST; this discovery provides new knowledge that may pave the way towards effective RSV therapeutics and new tool compounds to interrogate RSV L protein function.
Bioorg. Med. Chem. Lett., 2013, 23, 6789–6793.
|1548995||2-Oxa-7-azaspiro[3.5]nonane hemioxalate, 97%||1379811-94-5||Pricing|
■ 5+4]-spirocyclic compounds:
When 2-oxa-6-azaspiro-[3.4]octane was substituted in 4-anilinoquinazoline derivative, higher EGFR inhibitory activities against two lung cancer cell lines (HCC827 and A549) were observed.
Bioorg. Med. Chem. Lett., 2013, 23, 5385-5388
|1581759||2-Oxa-6-azaspiro[3.4]octane hemioxalate, 97%||1408075-00-2||Pricing|
■ [5+5]-spirocyclic compounds
These spiro-bicyclic compounds have been used in the synthesis of the analogues ofα4β2 nicotinic acetylcholine receptor agonist; they have been applied in the study of a potential treatment for cognitive deficits associated with psychiatric or neurological conditions.
J. Med. Chem., 2012, 55, 9181?9194
|434240||2-Azaspiro[4.4]nonane hemioxalate, 95%||1523617-88-0||Pricing|
|1586812||1-Benzyl-1,7-diazaspiro[4.4]nonane hemioxalate, 95%||128244-01-9||Pricing|
■ [4+4]-spirocyclic compounds:
Some azetidine derivatives have been synthesized and used in therapy and/or prophylaxis, in particular to inhibitors of soluble epoxide hydrolase (sEH). The compounds are useful for treating disease states mediated by sEH, including genitourinary disease states, pain disease states, respiratory disease states, neurological disease states, immunological disease states, inflammatory disease states, cancer, nephropathy, stroke, endothelial dysfunction, prevention of ischemic events and end organ protection.