Diethyl 4-(4-(2-(azepan-1-yl)ethoxy)-3-bromophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

ID: ALA4535978

PubChem CID: 155548011

Max Phase: Preclinical

Molecular Formula: C27H37BrN2O5

Molecular Weight: 549.51

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1c1ccc(OCCN2CCCCCC2)c(Br)c1

Standard InChI:  InChI=1S/C27H37BrN2O5/c1-5-33-26(31)23-18(3)29-19(4)24(27(32)34-6-2)25(23)20-11-12-22(21(28)17-20)35-16-15-30-13-9-7-8-10-14-30/h11-12,17,25,29H,5-10,13-16H2,1-4H3

Standard InChI Key:  ODHAYCRULKPRPQ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    5.3961   -7.3387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1001   -6.9007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8284   -7.2907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8542   -8.1128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1502   -8.5508    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6678   -6.9488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.5010   -6.0293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0723   -6.0751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3462   -5.6888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3183   -4.8630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0187   -4.4274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7470   -4.8172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.9908   -3.6017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2625   -3.2118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2368   -2.3897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5085   -1.9997    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5825   -8.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7236   -8.6001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2413   -6.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2566   -7.2433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9569   -6.8073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6847   -7.1957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5416   -7.4351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4480   -4.3824    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.8413   -2.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0422   -2.2646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5405   -1.1702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7118   -1.5088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9149   -0.6285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1022   -0.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
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 19 20  1  0
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 20 21  1  0
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  3 12  1  0
  5 22  1  0
  1 23  1  0
  9 24  1  0
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 24 28  1  0
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 21 32  1  0
 31 33  1  0
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 33 35  1  0
 34 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4535978

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 549.51

Molecular Weight (Monoisotopic): 548.1886

AlogP: 5.06

#Rotatable Bonds: 9

Polar Surface Area: 77.10

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 7.86

CX LogP: 4.51

CX LogD: 3.93

Aromatic Rings: 1

Heavy Atoms: 35

QED Weighted: 0.43

Np Likeness Score: -0.80

References

1. Malek R, Arribas RL, Palomino-Antolin A, Totoson P, Demougeot C, Kobrlova T, Soukup O, Iriepa I, Moraleda I, Diez-Iriepa D, Godyń J, Panek D, Malawska B, Głuch-Lutwin M, Mordyl B, Siwek A, Chabchoub F, Marco-Contelles J, Kiec-Kononowicz K, Egea J, de Los Ríos C, Ismaili L..  (2019)  New Dual Small Molecules for Alzheimer's Disease Therapy Combining Histamine H3 Receptor (H3R) Antagonism and Calcium Channels Blockade with Additional Cholinesterase Inhibition.,  62  (24): [PMID:31724859] [10.1021/acs.jmedchem.9b00937]

Source

Source(1):

• Scientific Literature