An azaspiro compound is a spiro compound in which at least one of the cyclic components is a nitrogen heterocyle.
| Member | Definition | Role |
|---|
| (3-chloro-1-benzothiophen-2-yl)-[2-(2-chloro-6-methylphenyl)imino-4-methylene-3-thia-1-azaspiro[4.5]decan-1-yl]methanone | | (3-chloro-1-benzothiophen-2-yl)-[2-(2-chloro-6-methylphenyl)imino-4-methylene-3-thia-1-azaspiro[4.5]decan-1-yl]methanone |
| (4-tert-butylphenyl)-[2-(4-fluorophenyl)-8-methyl-3-sulfanylidene-1,4,8-triazaspiro[4.5]dec-1-en-4-yl]methanone | | (4-tert-butylphenyl)-[2-(4-fluorophenyl)-8-methyl-3-sulfanylidene-1,4,8-triazaspiro[4.5]dec-1-en-4-yl]methanone |
| 1,4-dioxa-8-azaspiro[4.5]decan-8-yl-(3-methyl-2-benzofuranyl)methanone | | 1,4-dioxa-8-azaspiro[4.5]decan-8-yl-(3-methyl-2-benzofuranyl)methanone |
| 1,4-dioxa-8-azaspiro[4.5]decan-8-yl(4,5,6,7-tetrahydro-1-benzothiophen-2-yl)methanone | | 1,4-dioxa-8-azaspiro[4.5]decan-8-yl(4,5,6,7-tetrahydro-1-benzothiophen-2-yl)methanone |
| 2-(2,5-dichlorophenoxy)-1-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-1-butanone | | 2-(2,5-dichlorophenoxy)-1-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-1-butanone |
| 2-[(1-tert-butyl-5-tetrazolyl)-thiophen-2-ylmethyl]-2-azaspiro[5.5]undecane | | 2-[(1-tert-butyl-5-tetrazolyl)-thiophen-2-ylmethyl]-2-azaspiro[5.5]undecane |
| 2-amino-3-cyano-5-oxo-1'-spiro[7,8-dihydro-6H-1-benzopyran-4,4'-piperidine]carboxylic acid (phenylmethyl) ester | | 2-amino-3-cyano-5-oxo-1'-spiro[7,8-dihydro-6H-1-benzopyran-4,4'-piperidine]carboxylic acid (phenylmethyl) ester |
| 2',2'-dimethyl-3-spiro[5,6,7,8a-tetrahydrothiazolo[3,2-a]pyridine-8,4'-thiane]one | | 2',2'-dimethyl-3-spiro[5,6,7,8a-tetrahydrothiazolo[3,2-a]pyridine-8,4'-thiane]one |
| 4-(2-azaspiro[5.5]undecan-2-ylsulfonyl)-N-butan-2-ylbenzenesulfonamide | | 4-(2-azaspiro[5.5]undecan-2-ylsulfonyl)-N-butan-2-ylbenzenesulfonamide |
| 6-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-3-ethyl-1H-pyrimidine-2,4-dione | | 6-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-3-ethyl-1H-pyrimidine-2,4-dione |
| 6-methoxyspirotryprostatin b | An indole alkaloid isolated from a marine-derived fungal strain Aspergillus sydowii PFW1-13 and has been shown to exhibit cytotoxic activity. | 6-methoxyspirotryprostatin B |
| 8-(9-methyl-5H-pyrimido[5,4-b]indol-4-yl)-1,4-dioxa-8-azaspiro[4.5]decane | | 8-(9-methyl-5H-pyrimido[5,4-b]indol-4-yl)-1,4-dioxa-8-azaspiro[4.5]decane |
| asperparaline a | An alkaloid isolated from Aspergillus aculeatus. | asperparaline A |
| atogepant | A secondary carboxamide resulting from the formal condensation of the carboxy group of (3'S)-2'-oxo-1',2',5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3'-pyrrolo[2,3-b]pyridine]-3-carboxylic acid with the amino group of (3S,5S,6R)-3-amino-6-methyl-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-2-one. It is a selective oral, small-molecule antagonist of calcitonin gene-related peptide (CGRP) receptor that has been approved for the treatment of migraine. | atogepant |
| avapro | A biphenylyltetrazole that is an angiotensin II receptor antagonist used mainly for the treatment of hypertension. | irbesartan |
| AZD1979 | A carboxamide resulting from the formal condensation of the carboxy group of 5-(p-methoxyphenyl)-1,3,4-oxadiazole-2-carboxylic acid with the amino group of 3-phenoxyazetidine and in which the phenoxy group has been substituted at the para- position by a 2-oxa-6-azaspiro[3.3]heptan-6-ylmethyl group. It is a melanin concentrating hormone receptor 1 (MCHr1) antagonist. | AZD1979 |
| buspirone | An azaspiro compound that is 8-azaspiro[4.5]decane-7,9-dione substituted at the nitrogen atom by a 4-(piperazin-1-yl)butyl group which in turn is substituted by a pyrimidin-2-yl group at the N(4) position. | buspirone |
| CCT251545 | A chloropyridine that is 3-chloropyridine substituted by a 1-oxo-2,8-diazaspiro[4.5]decan-8-yl group and a 4-(1-methyl-1H-pyrazol-4-yl)phenyl group at positions 4 and 5, respectively. It is an orally bioavailable inhibitor of Wnt signaling (IC50 = 5 nM) and a potent and selective chemical probe for cyclin-dependent kinases CDK8 and CDK19. | CCT251545 |
| colibactin | A member of the class of 1,3-thiazoles that comprises of two units of 2-[(2-{6-[(2S)-2-methyl-3,4-dihydro-2H-pyrrol-5-yl]-5-oxo-4-azaspiro[2.4]hept-6-en-7-yl}acetamido)methyl]-1,3-thiazole-4-carboxylic acid linked together via the formal condensation of the carboxy groups. It is a secondary metabolite produced by certain strains of bacteria found in the human gut such as Escherichia coli. It has the ability to bind covalently to DNA and is strongly associated with colorectal cancer. | colibactin |
| delgocitinib | A pyrrolopyrimidine that is 7H-pyrrolo[2,3-d]pyrimidine substituted by a (3S,4R)-1-(cyanoacetyl)-3-methyl-1,6-diazaspiro[3.4]octan-6-yl group at position 4. It is a pan-Janus kinase (JAK) inhibitor and is approved for treatment of atopic dermatitis (AD) in Japan. | delgocitinib |
| derquantel | | derquantel |
| ecteinascidin 743 | A tetrahydroisoquinoline alkaloid obtained from a Caribbean tunicate Ecteinascidia turbinata. Used for the treatment of soft tissue sarcoma and relapsed ovarian cancer. | trabectedin |
| esculeoside a | A steroid saponin that is spirosolane-3,23,27-triol in which the hydroxy group at position 23 is acetylated and the hydroxy groups at positions 3 and 27 are glycosylated by lycotetraosyl and a beta-D-glucopyranosyl moieties respectively. Isolated from the fruits of Lycopersicon esculentum, it exhibits cytotoxic activity. | esculeoside A |
| fenspiride | | 8-(2-phenylethyl)-1-oxa-3,8-diazaspiro[4.5]decan-2-one |
| fumiquinazoline c | A fumiquinazoline obtained by oxidative spirocyclisation of fumiquinazoline A. | fumiquinazoline C |
| gabapentin-lactam | | 2-Azaspiro[4.5]decan-3-one |
| ledipasvir | A benzimidazole derivative that is used in combination with sofosbuvir (under the trade name Harvoni) for the treatment of chronic hepatitis C genotype 1 infection. | ledipasvir |
| liproxstatin-1 | An azaspiro compound that is 1'H-spiro[piperidine-4,2'-quinoxaline] in which the hydrogen at position 3' is replaced by a (3-chlorobenzyl)amino group. It is a potent inhibitor of ferroptosis. | liproxstatin-1 |
| lycoflexine | | Lycoflexine |
| marineosin a | A macrocycle isolated from a marine sediment-derived actinomycete, Streptomyces sp. It exhibits cytotoxicity against colon tumour cell lines. | marineosin A |
| marineosin b | A macrocycle isolated from a marine sediment-derived actinomycete, Streptomyces sp. A stereoisomer of marineosin A, it exhibits cytotoxicity against colon tumour cell lines. | marineosin B |
| mdl 72832 | | 8-[4-(2,3-dihydro-1,4-benzodioxin-3-ylmethylamino)butyl]-8-azaspiro[4.5]decane-7,9-dione |
| MI-63 | An azaspiro compound resulting from the formal fusion of position 3 of 6-chloro-oxindole with position 3 of (2R,3SS5S)-3-(3-chloro-2-fluorophenyl)-5-(2,2-dimethylpropyl)-N-[2-(morpholin-4-yl)ethyl]pyrrolidine-2-carboxamide. It is a potent inhibitor of the MDM2-p53 interaction. | MI-63 |
| mosapramine | A dibenzoazepine that is 10,11-dihydro-5H-dibenzo[b,f]azepine which is substituted by chlorine at position 3 and in which the hydrogen attached to the nitrogen is replaced by a 3-(2-oxohexahydro-2H-spiro[imidazo[1,2-a]pyridine-3,4'-piperidin]-1'-yl)propyl group. | 1'-[3-(3-chloro-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl]hexahydro-2H-spiro[imidazo[1,2-a]pyridine-3,4'-piperidin]-2-one |
| N-[2-(trifluoromethyl)-1,3-benzodioxol-2-yl]-1,4-dioxa-8-azaspiro[4.5]decane-8-carboxamide | | N-[2-(trifluoromethyl)-1,3-benzodioxol-2-yl]-1,4-dioxa-8-azaspiro[4.5]decane-8-carboxamide |
| phenylpropanolamine | | Fawcettimine |
| pseurotin | A spirocyclic that is 1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione bearing 1,2-dihydroxyhex-3-en-1-yl, methyl, methoxy, benzoyl and hydroxy substituents at positions 2, 3, 8, 8 and 9 respectively. | pseurotin A |
| remikiren | | Solamargine |
| rolapitant | An azaspiro compound that is 1,7-diazaspiro[4.5]decan-2-one carrying additional phenyl and 1-{[3,5-bis(trifluoromethyl)phenyl]ethoxy}methyl substituents at position 8. Used (in the form of the hydrochloride hydrate) for the prevention of delayed nausea and vomiting associated with initial and repeat courses of emetogenic cancer chemotherapy. | rolapitant |
| sb-224289 | A member of the class of benzamides obtained by formal condensation of the carboxy group of 2'-methyl-4'-(5-methyl-1,2,4-oxadiazol-3-yl)biphenyl-4-carboxylic acid with the secondary amino group of 1'-methyl-6,7-dihydro-5H-spiro[furo[2,3-f]indole-3,4'-piperidine]. Selective 5-HT1B receptor antagonist (pKi = 8.2). Displays >60-fold selectivity over 5-HT1D, 5-HT1A, 5-HT1E, 5-HT1F, 5-HT2A and 5-HT2C receptors in radioligand binding and functional assays. Centrally active following oral administration in vivo. | SB 224289 |
| solasodine | An oxaspiro compound and steroid alkaloid sapogenin with formula C27H43NO2 found in the Solanum (nightshade) family. It is used as a precursor in the synthesis of complex steroidal compounds such as contraceptive pills. | solasodine |
| sorbinil | An azaspiro compound having a monofluoro-substituted chromane skeleton spiro-linked to an imidazolidinedione ring. | sorbinil |
| spiperone | An azaspiro compound that is 1,3,8-triazaspiro[4.5]decane which is substituted at positions 1, 4, and 8 by phenyl, oxo, and 4-(p-fluorophenyl)-4-oxobutyl groups, respectively. | spiperone |
| spiramide | An azaspiro compound that consists of 1,3,8-triazaspiro[4.5]decan-4-one having a phenyl group attached to N-1 and a 3-(4-fluorophenoxy)propyl attached to N-8. Selective 5-HT antagonist, which binds to 5-HT2 sites as potently as spiperone but has lower affinity for 5-HT2C receptors. Also a high affinity D2 receptor antagonist (Ki = 3 nM). Lacks the disruptive effect of spiperone on animal behaviour. | spiramide |
| spirapril | | spirapril |
| spiraprilat | An azaspiro compound that is spirapril in which the ethyl ester group has been hydrolysed to the corresponding carboxylic acid group. It is the active metabolite of the angiotensin-converting enzyme (ACE) inhibitor spirapril. | spiraprilat |
| spiroiminodihydantoin | An azaspiro compound that is 1,3,6,8-tetraazaspiro[4.4]non-6-ene which is substituted by oxo groups at positions 2, 4, and 9. Both enantiomers are highly mutagenic products resulting from the oxidation of guanine and 8-oxo-7,8-dihydroguanine in DNA by reactive oxygen species. | spiroiminodihydantoin |
| tomatidine | A 3beta-hydroxy steroid resulting from the substitution of the 3beta-hydrogen of tomatidane by a hydroxy group. | tomatidine |