(+/-)-1-{(4-chlorophenyl)[4-(pyrrolidin-1-ylmethyl)phenyl]phenylmethyl}-1H-imidazole

ID: ALA218577

Chembl Id: CHEMBL218577

PubChem CID: 16108917

Max Phase: Preclinical

Molecular Formula: C27H26ClN3

Molecular Weight: 427.98

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Clc1ccc(C(c2ccccc2)(c2ccc(CN3CCCC3)cc2)n2ccnc2)cc1

Standard InChI:  InChI=1S/C27H26ClN3/c28-26-14-12-25(13-15-26)27(31-19-16-29-21-31,23-6-2-1-3-7-23)24-10-8-22(9-11-24)20-30-17-4-5-18-30/h1-3,6-16,19,21H,4-5,17-18,20H2

Standard InChI Key:  IAQQCLOGRBFIBC-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA218577

   1H-Imidazole,1-[(4-chlorophenyl)phenyl[4-(1-pyrrolidinylmethyl)phenyl]methyl]-

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: 427.98

Molecular Weight (Monoisotopic): 427.1815

AlogP: 5.97

#Rotatable Bonds: 6

Polar Surface Area: 21.06

Molecular Species: BASE

HBA: 3

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.25

CX LogP: 6.19

CX LogD: 4.31

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.35

Np Likeness Score: -0.91

References

1. Gemma S, Campiani G, Butini S, Kukreja G, Joshi BP, Persico M, Catalanotti B, Novellino E, Fattorusso E, Nacci V, Savini L, Taramelli D, Basilico N, Morace G, Yardley V, Fattorusso C..  (2007)  Design and synthesis of potent antimalarial agents based on clotrimazole scaffold: exploring an innovative pharmacophore.,  50  (4): [PMID:17263523] [10.1021/jm061429p]

2. Gemma S, Campiani G, Butini S, Kukreja G, Coccone SS, Joshi BP, Persico M, Nacci V, Fiorini I, Novellino E, Fattorusso E, Taglialatela-Scafati O, Savini L, Taramelli D, Basilico N, Parapini S, Morace G, Yardley V, Croft S, Coletta M, Marini S, Fattorusso C..  (2008)  Clotrimazole scaffold as an innovative pharmacophore towards potent antimalarial agents: design, synthesis, and biological and structure-activity relationship studies.,  51  (5): [PMID:18278860] [10.1021/jm701247k]

3. Gemma S, Campiani G, Butini S, Joshi BP, Kukreja G, Coccone SS, Bernetti M, Persico M, Nacci V, Fiorini I, Novellino E, Taramelli D, Basilico N, Parapini S, Yardley V, Croft S, Keller-Maerki S, Rottmann M, Brun R, Coletta M, Marini S, Guiso G, Caccia S, Fattorusso C..  (2009)  Combining 4-aminoquinoline- and clotrimazole-based pharmacophores toward innovative and potent hybrid antimalarials.,  52  (2): [PMID:19113955] [10.1021/jm801352s]

4. Gemma S, Camodeca C, Sanna Coccone S, Joshi BP, Bernetti M, Moretti V, Brogi S, Bonache de Marcos MC, Savini L, Taramelli D, Basilico N, Parapini S, Rottmann M, Brun R, Lamponi S, Caccia S, Guiso G, Summers RL, Martin RE, Saponara S, Gorelli B, Novellino E, Campiani G, Butini S..  (2012)  Optimization of 4-aminoquinoline/clotrimazole-based hybrid antimalarials: further structure-activity relationships, in vivo studies, and preliminary toxicity profiling.,  55  (15): [PMID:22783984] [10.1021/jm300802s]

Source

Source(1):

• Scientific Literature