2-[2-(6-Methoxy-1,3,3a,4,5,9b-hexahydro-benzo[e]isoindol-2-yl)-ethyl]-4H-9-thia-2,4,5-triaza-fluorene-1,3-dione

ID: ALA40650

Chembl Id: CHEMBL40650

Cas Number: 181490-18-6

PubChem CID: 10527469

Max Phase: Preclinical

Molecular Formula: C24H24N4O3S

Molecular Weight: 448.55

Molecule Type: Small molecule

Names and Identifiers

Synonyms: A-131701 | A-131701|CHEMBL40650|2-[2-(6-Methoxy-1,3,3a,4,5,9b-hexahydro-benzo[e]isoindol-2-yl)-ethyl]-4H-9-thia-2,4,5-triaza-fluorene-1,3-dione|SCHEMBL7637490|BDBM50060965|181490-18-6|A 131701|2-[2-((3aR,9bR)-6-Methoxy-1,3,3a,4,5,9b-hexahydro-benzo[e]isoindol-2-yl)-ethyl]-4H-9-thia-2,4,5-triaza-fluorene-1,3-dione|2-[2-((3aR,9bR)-6-Methoxy-1,3,3a,4,5,9b-hexahydro-benzo[e]isoindol-2-yl)-ethyl]-4H-9-thia-2,4,6-triaza-fluorene-1,3-dione|5-[2-[(3Ar,9bR)-6-methoxy-1,3,3a,4,5,9b-hexahydrobenzo[e]isoindShow More⌵

Canonical SMILES:  COc1cccc2c1CC[C@H]1CN(CCn3c(=O)[nH]c4c(sc5cccnc54)c3=O)C[C@@H]21

Standard InChI:  InChI=1S/C24H24N4O3S/c1-31-18-5-2-4-15-16(18)8-7-14-12-27(13-17(14)15)10-11-28-23(29)22-21(26-24(28)30)20-19(32-22)6-3-9-25-20/h2-6,9,14,17H,7-8,10-13H2,1H3,(H,26,30)/t14-,17+/m0/s1

Standard InChI Key:  OLPQNRLJYOGSGV-WMLDXEAASA-N

Alternative Forms

1. Parent:

   

   ALA40650

   2-[2-(6-Methoxy-1,3,3a,4,5,9b-hexahydro-benzo[e]isoindol-2-yl)-ethyl]-4H-9-thia-2,4,5-triaza-fluorene-1,3-dione

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: 448.55

Molecular Weight (Monoisotopic): 448.1569

AlogP: 2.97

#Rotatable Bonds: 4

Polar Surface Area: 80.22

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.50

CX Basic pKa: 8.27

CX LogP: 3.98

CX LogD: 3.05

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.52

Np Likeness Score: -0.98

References

1. Meyer MD, Altenbach RJ, Basha FZ, Carroll WA, Condon S, Elmore SW, Kerwin JF, Sippy KB, Tietje K, Wendt MD, Hancock AA, Brune ME, Buckner SA, Drizin I..  (2000)  Structure-activity studies for a novel series of tricyclic substituted hexahydrobenz[e]isoindole alpha(1A) adrenoceptor antagonists as potential agents for the symptomatic treatment of benign prostatic hyperplasia (BPH).,  43  (8): [PMID:10780916] [10.1021/jm990567u]

2. Meyer MD, Altenbach RJ, Basha FZ, Carroll WA, Drizin I, Elmore SW, Ehrlich PP, Lebold SA, Tietje K, Sippy KB, Wendt MD, Plata DJ, Plagge F, Buckner SA, Brune ME, Hancock AA, Kerwin JF..  (1997)  Synthesis and pharmacological characterization of 3-[2-((3aR,9bR)-cis-6-methoxy-2,3,3a,4,5,9b-hexahydro-1H-benz[e] isoindol-2-yl)ethyl]pyrido-[3',4':4,5]thieno[3,2-d]pyrimidine-2,4 (1H,3H)-dione (A-131701): a uroselective alpha 1A adrenoceptor antagonist for the symptomatic treatment of benign prostatic hyperplasia.,  40  (20): [PMID:9379432] [10.1021/jm970364a]

3. Li MY, Tsai KC, Xia L..  (2005)  Pharmacophore identification of alpha(1A)-adrenoceptor antagonists.,  15  (3): [PMID:15664832] [10.1016/j.bmcl.2004.11.032]

4. Vistoli G, Pedretti A, Villa L, Testa B..  (2005)  Range and sensitivity as descriptors of molecular property spaces in dynamic QSAR analyses.,  48  (15): [PMID:16033273] [10.1021/jm0408969]

Source

Source(1):

• Scientific Literature