N-{5-[2-(1-Pyrrolidinesulfamoyl)-4,5-dimethoxy-benzyl]-1,3,4-thiadiazol-2-yl}-N-phenylamine.

ID: ALA2270945

PubChem CID: 46177208

Max Phase: Preclinical

Molecular Formula: C21H24N4O4S2

Molecular Weight: 460.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(Cc2nnc(Nc3ccccc3)s2)c(S(=O)(=O)N2CCCC2)cc1OC

Standard InChI:  InChI=1S/C21H24N4O4S2/c1-28-17-12-15(13-20-23-24-21(30-20)22-16-8-4-3-5-9-16)19(14-18(17)29-2)31(26,27)25-10-6-7-11-25/h3-5,8-9,12,14H,6-7,10-11,13H2,1-2H3,(H,22,24)

Standard InChI Key:  TZGRJDHCXAWFQV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    4.3605  -13.3193    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.1776  -13.3180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7679  -12.6109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2355  -12.0927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2344  -12.9123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9424  -13.3212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6521  -12.9118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6493  -12.0891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9407  -11.6839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5264  -13.3203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8190  -12.9112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5277  -11.6843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5275  -10.8671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3617  -14.1365    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3554  -11.6779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3342  -10.8570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9827  -10.3608    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.7102   -9.5904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -9.6114    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6610  -10.3949    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1687   -8.9150    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9859   -8.9057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3966   -9.6091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2077   -9.5967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6132   -8.8865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1906   -8.1802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3798   -8.1954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7012  -14.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550  -15.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7722  -15.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0234  -14.6169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  1  3  2  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  5 10  1  0
 10 11  1  0
  4 12  1  0
 12 13  1  0
  7  1  1  0
  1 14  1  0
  8 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 16  2  0
 18 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 14 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2270945

   5-[(4,5-dimethoxy-2-pyrrolidin-1-ylsulfonylphenyl)methyl]-N-phenyl-1,3,4-thiadiazol-2-amine

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: 460.58

Molecular Weight (Monoisotopic): 460.1239

AlogP: 3.67

#Rotatable Bonds: 8

Polar Surface Area: 93.65

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.70

CX Basic pKa: 0.60

CX LogP: 2.97

CX LogD: 2.97

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.55

Np Likeness Score: -1.77

References

1. Camoutsis C, Geronikaki A, Ciric A, Soković M, Zoumpoulakis P, Zervou M..  (2010)  Sulfonamide-1,2,4-thiadiazole derivatives as antifungal and antibacterial agents: synthesis, biological evaluation, lipophilicity, and conformational studies.,  58  (2): [PMID:20118573] [10.1248/cpb.58.160]

Source

Source(1):

• Scientific Literature