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Spirocyclic Compounds

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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

structure Product no. description cas pricing
912509 8-Benzyl-2,8-diazaspiro[4.5]decane, 95% 336191-15-2 Pricing
1117680 8-Methyl-2,8-diazaspiro[4.5]decane, 95% 1158750-98-1 Pricing
1117933 2,8-Diazaspiro[4.5]decan-3-one, 95% 561314-57-6 Pricing
1558751 8-Benzyl-2,8-diazaspiro[4.5]decan-3-one, 95% 154495-69-9 Pricing
328108 2-Boc-2,8-diazaspiro[4.5]decane hemioxalate, 95% 336191-17-4 Pricing
1549294 2-Benzyl-2,8-diazaspiro[4.5]decane hemioxalate, 95% 867009-61-8 Pricing
1139418 8-Boc-2,8-diazaspiro[4.5]decane oxalate, 95% 236406-39-6 Pricing
1175510 2-Azaspiro[4.5]decane hemioxlate, 95% 176-66-9 Pricing
1019223 1'-Boc-spiro[indoline-3,4'-piperidine], 96% 180465-84-3 Pricing
908679 8-Oxa-2-azaspiro[4.5]decane hemioxlate, 95% 310-93-0 Pricing
1139419 2-Methyl-2,8-diazaspiro[4.5]decane hemioxalate, 95% 1061873-16-2 Pricing
1711618 7-Benzyl-2,7-diazaspiro[4,5]decane hemioxalate, 95% 1086395-18-7 Pricing
1711617 7-Benzyl-2,7-diazaspiro[4,5]decan-3-one hemioxlate, 95% 1312760-55-6 Pricing
1586814 1-(2,8-Diazaspiro[4.5]decan-2-yl)ethanone hemioxalate, 95% 870082-43-2 Pricing
511395 4,4-Pentamethylene-2-pyrrolidinone, 98% 64744-50-9 Pricing

■ [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

structure Product no. description cas pricing
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.

structure Product no. description cas pricing
1350800 7-Boc-2-oxo-7-azaspiro[3.5]nonane, 95% 203661-69-2 Pricing
1548995 2-Oxa-7-azaspiro[3.5]nonane hemioxalate, 97% 1379811-94-5 Pricing
1494423 7-Boc-1-oxa-7-azaspiro[3.5]nonane, 96% 864684-96-8 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

structure Product no. description cas pricing
1238567 2-Oxa-6-azaspiro[3.4]octan-7-one, 95% 1207174-87-5 Pricing
1581815 2-Benzyl-2,6-diazaspiro[3.4]octan-7-one, 95% 1392211-22-1 Pricing
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

structure Product no. description cas pricing
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.

structure Product no. description cas pricing
1565862 6-[(4-Methylphenyl)sulfonyl]-1-benzyl-1,6-diazaspiro[3.3]heptan-2-one, 95% 1263296-91-8 Pricing
1351261 1-Benzyl-1,6-diazaspiro[3.3]heptane hemioxalate, 95% 1223573-42-9 Pricing
1556975 1-Benzyl-6-oxa-1-azaspiro[3.3]heptane, 95% 1223573-38-3 Pricing
1238560 6-Oxa-1-azaspiro[3.3]heptane hemioxalate, 95% 1046153-00-7 Pricing
1565863 6-[(4-Methylphenyl)sulfonyl]-1-benzyl-1,6-diazaspiro[3.3]heptane, 95% 1223573-36-1 Pricing
1351260 6-Boc-1,6-diazaspiro[3.3]heptane hemioxalate, 95% 1431868-60-8 Pricing
1590282 6-[(4-Methylphenyl)sulfonyl]-1,6-diazaspiro[3.3]heptane, 95% 1223573-45-2 Pricing