1-(sec-butylamino)-3-(3,6-dichloro-9H-carbazol-9-yl)propan-2-ol

ID: ALA3359320

PubChem CID: 2879322

Max Phase: Preclinical

Molecular Formula: C19H22Cl2N2O

Molecular Weight: 365.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(C)NCC(O)Cn1c2ccc(Cl)cc2c2cc(Cl)ccc21

Standard InChI:  InChI=1S/C19H22Cl2N2O/c1-3-12(2)22-10-15(24)11-23-18-6-4-13(20)8-16(18)17-9-14(21)5-7-19(17)23/h4-9,12,15,22,24H,3,10-11H2,1-2H3

Standard InChI Key:  CRSBMRJNJIXPFW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    4.0504   -5.1695    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7211   -5.6572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4620   -6.4405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0101   -7.0545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8177   -6.8866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0740   -6.0990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5241   -5.4884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6370   -6.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3843   -5.6582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5798   -5.4861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0273   -6.0978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2849   -6.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0886   -7.0528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3694   -7.5023    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7332   -7.5002    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.0486   -4.3427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7638   -3.9278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7619   -3.1010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4806   -4.3396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4770   -2.6861    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4753   -1.8593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1904   -1.4444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7584   -1.4474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7567   -0.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  3  1  0
  2  1  1  0
  1  9  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  5 14  1  0
 12 15  1  0
  1 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3359320

   1-(Butan-2-ylamino)-3-(3,6-dichlorocarbazol-9-yl)propan-2-ol

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: 365.30

Molecular Weight (Monoisotopic): 364.1109

AlogP: 4.85

#Rotatable Bonds: 6

Polar Surface Area: 37.19

Molecular Species: BASE

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.09

CX LogP: 4.82

CX LogD: 2.24

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.66

Np Likeness Score: -0.91

References

1. Liebens V, Gerits E, Knapen WJ, Swings T, Beullens S, Steenackers HP, Robijns S, Lippell A, O'Neill AJ, Veber M, Fröhlich M, Krona A, Lövenklev M, Corbau R, Marchand A, Chaltin P, De Brucker K, Thevissen K, Cammue BP, Fauvart M, Verstraeten N, Michiels J..  (2014)  Identification and characterization of an anti-pseudomonal dichlorocarbazol derivative displaying anti-biofilm activity.,  24  (23): [PMID:25453797] [10.1016/j.bmcl.2014.10.039]

2. 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]

3. Johannes Zuegg, Alysha Elliott, Maite Amado, Emma Cowie, Ali Hinton, Geraldine Kaeslin, Angela Kavanagh, Anne Kunert, Gabriell Lowe, Soumya Ramu, Janet Reid, Robin Trauer, Mathilde Desselle, Ruth Neale, Karl Hansford, Mark Blascovich, Matthew Cooper. CO-ADD screening of MMV (CH) - Pandemic Response Box,  [10.6019/CHEMBL4513161]

4. Schrank CL, Wilt IK, Monteagudo Ortiz C, Haney BA, Wuest WM..  (2021)  Using membrane perturbing small molecules to target chronic persistent infections.,  12  (8.0): [PMID:34458737] [10.1039/D1MD00151E]

5. 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(2):

• Scientific Literature
• CO-ADD antimicrobial screening data