5-Allyl-10-methoxy-2,2,4-trimethyl-2,5-dihydro-1H-6-oxa-1-aza-chrysene

ID: ALA266282

Chembl Id: CHEMBL266282

Cas Number: 239066-73-0

PubChem CID: 9906282

Max Phase: Preclinical

Molecular Formula: C23H25NO2

Molecular Weight: 347.46

Molecule Type: Small molecule

Names and Identifiers

Synonyms: AL-438 | AL-438|239066-73-0|CHEMBL266282|5-allyl-10-methoxy-2,2,4-trimethyl-2,5-dihydro-1H-chromeno[3,4-f]quinoline|10-methoxy-2,2,4-trimethyl-5-prop-2-enyl-1,5-dihydrochromeno[3,4-f]quinoline|AL-43|SCHEMBL4172433|BDBM50107347|AKOS040745539|HY-114154|CS-0077158|A-224817.0|A-240610.0|5-Allyl-10-methoxy-2,2,4-trimethyl-2,5-dihydro-1H-6-oxa-1-aza-chrysene|(+)5-Allyl-10-methoxy-2,2,4-trimethyl-2,5-dihydro-1H-6-oxa-1-aza-chrysene|(+/-)5-Allyl-10-methoxy-2,2,4-trimethyl-2,5-dihydro-1H-6-oxa-1-aza-chryShow More⌵

Synonyms from Alternative Forms(1): AL-438

Canonical SMILES:  C=CCC1Oc2cccc(OC)c2-c2ccc3c(c21)C(C)=CC(C)(C)N3

Standard InChI:  InChI=1S/C23H25NO2/c1-6-8-18-22-15(21-17(25-5)9-7-10-19(21)26-18)11-12-16-20(22)14(2)13-23(3,4)24-16/h6-7,9-13,18,24H,1,8H2,2-5H3

Standard InChI Key:  CZSDJYXNNJQXBB-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA266282

   AL-43

2. Alternative Forms:

   

   ALA266282

   10-(111C)methoxy-2,2,4-trimethyl-5-prop-2-enyl-1,5-dihydrochromeno[3,4-f]quinoline

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 347.46

Molecular Weight (Monoisotopic): 347.1885

AlogP: 5.98

#Rotatable Bonds: 3

Polar Surface Area: 30.49

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 3.42

CX LogP: 4.97

CX LogD: 4.97

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.69

Np Likeness Score: 0.78

References

1. Kym PR, Kort ME, Coghlan MJ, Moore JL, Tang R, Ratajczyk JD, Larson DP, Elmore SW, Pratt JK, Stashko MA, Falls HD, Lin CW, Nakane M, Miller L, Tyree CM, Miner JN, Jacobson PB, Wilcox DM, Nguyen P, Lane BC..  (2003)  Nonsteroidal selective glucocorticoid modulators: the effect of C-10 substitution on receptor selectivity and functional potency of 5-allyl-2,5-dihydro-2,2,4-trimethyl-1H-[1]benzopyrano[3,4-f]quinolines.,  46  (6): [PMID:12620078] [10.1021/jm020335m]

2. Elmore SW, Pratt JK, Coghlan MJ, Mao Y, Green BE, Anderson DD, Stashko MA, Lin CW, Falls D, Nakane M, Miller L, Tyree CM, Miner JN, Lane B..  (2004)  Differentiation of in vitro transcriptional repression and activation profiles of selective glucocorticoid modulators.,  14  (7): [PMID:15026058] [10.1016/j.bmcl.2004.01.044]

3. Elmore SW, Pratt JK, Coghlan MJ, Mao Y, Green BE, Anderson DD, Stashko MA, Lin CW, Falls D, Nakane M, Miller L, Tyree CM, Miner JN, Lane B..  (2004)  Differentiation of in vitro transcriptional repression and activation profiles of selective glucocorticoid modulators.,  14  (7): [PMID:15026058] [10.1016/j.bmcl.2004.01.044]

4. Elmore SW, Coghlan MJ, Anderson DD, Pratt JK, Green BE, Wang AX, Stashko MA, Lin CW, Tyree CM, Miner JN, Jacobson PB, Wilcox DM, Lane BC..  (2001)  Nonsteroidal selective glucocorticoid modulators: the effect of C-5 alkyl substitution on the transcriptional activation/repression profile of 2,5-dihydro-10-methoxy-2,2,4-trimethyl-1H-[1]benzopyrano[3,4-f]quinolines.,  44  (25): [PMID:11728194] [10.1021/jm010367u]

5. Elmore SW, Coghlan MJ, Anderson DD, Pratt JK, Green BE, Wang AX, Stashko MA, Lin CW, Tyree CM, Miner JN, Jacobson PB, Wilcox DM, Lane BC..  (2001)  Nonsteroidal selective glucocorticoid modulators: the effect of C-5 alkyl substitution on the transcriptional activation/repression profile of 2,5-dihydro-10-methoxy-2,2,4-trimethyl-1H-[1]benzopyrano[3,4-f]quinolines.,  44  (25): [PMID:11728194] [10.1021/jm010367u]

6. Elmore SW, Coghlan MJ, Anderson DD, Pratt JK, Green BE, Wang AX, Stashko MA, Lin CW, Tyree CM, Miner JN, Jacobson PB, Wilcox DM, Lane BC..  (2001)  Nonsteroidal selective glucocorticoid modulators: the effect of C-5 alkyl substitution on the transcriptional activation/repression profile of 2,5-dihydro-10-methoxy-2,2,4-trimethyl-1H-[1]benzopyrano[3,4-f]quinolines.,  44  (25): [PMID:11728194] [10.1021/jm010367u]

7. Wuest F, Kniess T, Bergmann R, Henry B, Pietzsch J..  (2007)  Synthesis and radiopharmacological characterization of [11C]AL-438 as a nonsteroidal ligand for imaging brain glucocorticoid receptors.,  17  (14): [PMID:17499506] [10.1016/j.bmcl.2007.04.094]

Source

Source(1):

• Scientific Literature