(S)-3-Chloro-2-fluoro-N-{1-[2-(2-isopropoxyphenoxy)ethyl]pyrrolidin-3-yl}benzenesulfonamide

ID: ALA3971046

PubChem CID: 134153796

Max Phase: Preclinical

Molecular Formula: C21H26ClFN2O4S

Molecular Weight: 456.97

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)Oc1ccccc1OCCN1CC[C@H](NS(=O)(=O)c2cccc(Cl)c2F)C1

Standard InChI:  InChI=1S/C21H26ClFN2O4S/c1-15(2)29-19-8-4-3-7-18(19)28-13-12-25-11-10-16(14-25)24-30(26,27)20-9-5-6-17(22)21(20)23/h3-9,15-16,24H,10-14H2,1-2H3/t16-/m0/s1

Standard InChI Key:  BMLCZHZOUFWRGB-INIZCTEOSA-N

Molfile:  

     RDKit          2D

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    3.4004  -13.0406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9830  -12.4602    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.1912  -12.2465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3880  -11.7527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9717  -11.0473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3712  -10.3369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1925  -10.3288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6088  -11.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2039  -11.7436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1504  -11.0555    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.3919  -13.1751    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2104  -13.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7011  -12.5174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4945  -12.7638    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4945  -13.5823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7011  -13.8266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1501  -12.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8850  -12.6281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5426  -12.1376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2569  -12.5523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2431  -13.3727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9326  -13.7829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6660  -13.4048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6861  -12.5851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9666  -12.1387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5355  -13.7829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5268  -14.5765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9551   -9.6336    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.8146  -14.9773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2299  -14.9928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  4  9  2  0
  5 10  1  0
  4  2  1  0
  2 11  1  0
 12 11  1  6
 13 12  1  0
 14 13  1  0
 14 15  1  0
 16 15  1  0
 12 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 20 25  2  0
 21 26  1  0
 26 27  1  0
  6 28  1  0
 27 29  1  0
 27 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3971046

   ---

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: 456.97

Molecular Weight (Monoisotopic): 456.1286

AlogP: 3.70

#Rotatable Bonds: 9

Polar Surface Area: 67.87

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.05

CX Basic pKa: 6.80

CX LogP: 3.52

CX LogD: 3.59

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.62

Np Likeness Score: -1.92

References

1. Rak A, Canale V, Marciniec K, Żmudzki P, Kotańska M, Knutelska J, Siwek A, Stachowicz G, Bednarski M, Nowiński L, Zygmunt M, Zajdel P, Sapa J..  (2016)  Arylsulfonamide derivatives of (aryloxy)ethyl pyrrolidines and piperidines as α1-adrenergic receptor antagonist with uro-selective activity.,  24  (21): [PMID:27658792] [10.1016/j.bmc.2016.09.017]

Source

Source(1):

• Scientific Literature