4-(5,6,7,8-Tetrahydro-imidazo[1,5-a]pyridin-5-yl)-benzonitrile

ID: ALA287677

Chembl Id: CHEMBL287677

Cas Number: 102676-87-9

PubChem CID: 9815923

Max Phase: Phase

Molecular Formula: C14H13N3

Molecular Weight: 223.28

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Fadrozole, (r)- | R-Fadrozole | Dexfadrostat|(R)-Fadrozole|Fadrozole, (R)-|R-FADROZOLE|(+)-Fadrozole|Dexfadrostat [INN]|102676-87-9|IC1B8751F6|UNII-IC1B8751F6|CHEMBL287677|4-[(5r)-5,6,7,8-Tetrahydroimidazo[1,5-A]pyridin-5-Yl]benzonitrile|(R)-4-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)benzonitrile|4-((5R)-5,6,7,8-Tetrahydroimidazo(1,5-a)pyridin-5-yl)benzonitrile|Benzonitrile, 4-((5R)-5,6,7,8-tetrahydroimidazo(1,5-a)pyridin-5-yl)-|Benzonitrile, 4-(5,6,7,8-tetrahydroimidazo(1,5-a)pyridin-5-yl)Show More⌵

Canonical SMILES:  N#Cc1ccc([C@H]2CCCc3cncn32)cc1

Standard InChI:  InChI=1S/C14H13N3/c15-8-11-4-6-12(7-5-11)14-3-1-2-13-9-16-10-17(13)14/h4-7,9-10,14H,1-3H2/t14-/m1/s1

Standard InChI Key:  CLPFFLWZZBQMAO-CQSZACIVSA-N

Alternative Forms

1. Parent:

   

   ALA287677

   DEXFADROSTAT

2. Alternative Forms:

   

   ALA287677

   Dexfadrostat hydrochloride

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 223.28

Molecular Weight (Monoisotopic): 223.1109

AlogP: 2.68

#Rotatable Bonds: 1

Polar Surface Area: 41.61

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.87

CX LogP: 2.41

CX LogD: 2.33

Aromatic Rings: 2

Heavy Atoms: 17

QED Weighted: 0.75

Np Likeness Score: -0.71

References

1. Furet P, Batzl C, Bhatnagar A, Francotte E, Rihs G, Lang M..  (1993)  Aromatase inhibitors: synthesis, biological activity, and binding mode of azole-type compounds.,  36  (10): [PMID:8496907] [10.1021/jm00062a012]

2. Cavalli A, Bisi A, Bertucci C, Rosini C, Paluszcak A, Gobbi S, Giorgio E, Rampa A, Belluti F, Piazzi L, Valenti P, Hartmann RW, Recanatini M..  (2005)  Enantioselective nonsteroidal aromatase inhibitors identified through a multidisciplinary medicinal chemistry approach.,  48  (23): [PMID:16279787] [10.1021/jm058042r]

3. Roumen L, Peeters JW, Emmen JM, Beugels IP, Custers EM, de Gooyer M, Plate R, Pieterse K, Hilbers PA, Smits JF, Vekemans JA, Leysen D, Ottenheijm HC, Janssen HM, Hermans JJ..  (2010)  Synthesis, biological evaluation, and molecular modeling of 1-benzyl-1H-imidazoles as selective inhibitors of aldosterone synthase (CYP11B2).,  53  (4): [PMID:20121113] [10.1021/jm901356d]

4. Adams CM, Hu CW, Jeng AY, Karki R, Ksander G, Lasala D, Leung-Chu J, Liang G, Liu Q, Meredith E, Rao C, Rigel DF, Shi J, Smith S, Springer C, Zhang C..  (2010)  The discovery of potent inhibitors of aldosterone synthase that exhibit selectivity over 11-beta-hydroxylase.,  20  (15): [PMID:20615692] [10.1016/j.bmcl.2010.06.086]

5. Meredith EL, Ksander G, Monovich LG, Papillon JP, Liu Q, Miranda K, Morris P, Rao C, Burgis R, Capparelli M, Hu QY, Singh A, Rigel DF, Jeng AY, Beil M, Fu F, Hu CW, LaSala D..  (2013)  Discovery and in Vivo Evaluation of Potent Dual CYP11B2 (Aldosterone Synthase) and CYP11B1 Inhibitors.,  4  (12): [PMID:24900631] [10.1021/ml400324c]

6. Hu Q, Yin L, Hartmann RW..  (2014)  Aldosterone synthase inhibitors as promising treatments for mineralocorticoid dependent cardiovascular and renal diseases.,  57  (12): [PMID:24422519] [10.1021/jm401430e]

7. Meguro M, Miyauchi S, Kanao Y, Naito S, Suzuki K, Inoue S, Yamada K, Homma T, Chiba K, Nara F, Furuzono S..  (2017)  4-Anilino-pyrimidine, novel aldosterone synthase (CYP11B2) inhibitors bearing pyrimidine structures.,  27  (9): [PMID:28359792] [10.1016/j.bmcl.2017.03.034]

8. Meyers K, Cogan DA, Burke J, Arenas R, Balestra M, Brown NF, Chen Z, Cerny MA, Clifford HE, Colombo F, Fader L, Frederick KS, Guo X, Goldberg D, Hornberger KR, Kugler S, Lord J, Marshall DR, Moss N, Parmentier JH, Richman JR, Schmenk J, Weldon SM, Yu M, Zhang M..  (2018)  Dihydrobenzisoxazole-4-one compounds are novel selective inhibitors of aldosterone synthase (CYP11B2) with in vivo activity.,  28  (5): [PMID:29254646] [10.1016/j.bmcl.2017.12.015]

9. International Nonproprietary Names for Pharmaceutical Substances (INN), 

10. Yin L, Pan Y, Xue Y, Chen X, You T, Huang J, Xu Q, Hu Q..  (2022)  Design, Synthesis, and Biological Evaluations of Pyridyl 4,5,6,7-Tetrahydro-4,7-Methanobenzo[d]isoxazoles as Potent and Selective Inhibitors of 11β-Hydroxylase.,  65  (17.0): [PMID:35975976] [10.1021/acs.jmedchem.2c01037]

Source

Source(2):

• Scientific Literature
• International Nonproprietary Names