1-(3,6-dichloro-9H-carbazol-9-yl)-3-morpholinopropan-2-ol

ID: ALA4548520

Cas Number: 253448-97-4

PubChem CID: 2802125

Max Phase: Preclinical

Molecular Formula: C19H20Cl2N2O2

Molecular Weight: 379.29

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  OC(CN1CCOCC1)Cn1c2ccc(Cl)cc2c2cc(Cl)ccc21

Standard InChI:  InChI=1S/C19H20Cl2N2O2/c20-13-1-3-18-16(9-13)17-10-14(21)2-4-19(17)23(18)12-15(24)11-22-5-7-25-8-6-22/h1-4,9-10,15,24H,5-8,11-12H2

Standard InChI Key:  MQIMMVBJAICTOC-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   21.4009  -19.4637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6894  -19.0624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7205  -18.2421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4504  -17.8624    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9828  -19.4782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9918  -20.2994    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.3321  -20.7860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5951  -21.5632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0529  -22.1784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2477  -22.0163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7055  -22.6315    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   17.9889  -21.2391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5311  -20.6239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4163  -21.5543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6585  -20.7730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4583  -20.5936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0158  -21.1954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7695  -21.9807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3270  -22.5825    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   20.9697  -22.1602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1397  -18.3056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8673  -17.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9076  -17.1071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2140  -16.6627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4801  -17.0404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
  7 13  1  0
  8 14  1  0
 14 15  2  0
  6 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 14 20  1  0
  4 21  1  0
  4 25  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4548520

   1-(3,6-Dichloro-carbazol-9-yl)-3-morpholin-4-yl-propan-2-ol

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: 379.29

Molecular Weight (Monoisotopic): 378.0902

AlogP: 3.79

#Rotatable Bonds: 4

Polar Surface Area: 37.63

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.44

CX LogP: 3.69

CX LogD: 3.37

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.75

Np Likeness Score: -1.20

References

1. Wang T, Mäser P, Picard D..  (2016)  Inhibition of Plasmodium falciparum Hsp90 Contributes to the Antimalarial Activities of Aminoalcohol-carbazoles.,  59  (13): [PMID:27312008] [10.1021/acs.jmedchem.6b00591]

2. Clausen JD, Kjellerup L, Cohrt KO, Hansen JB, Dalby-Brown W, Winther AL..  (2017)  Elucidation of antimicrobial activity and mechanism of action by N-substituted carbazole derivatives.,  27  (19): [PMID:28893470] [10.1016/j.bmcl.2017.08.067]

Source

Source(1):

• Scientific Literature