N-{5-[2-(4-Methylpiperazinesulfamoyl)-4,5-dimethoxy-benzyl]-1,3,4-thiadiazol-2-yl}-N-(p-chlorophenyl)amine

ID: ALA2270952

PubChem CID: 46177285

Max Phase: Preclinical

Molecular Formula: C22H26ClN5O4S2

Molecular Weight: 524.07

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(Cc2nnc(Nc3ccc(Cl)cc3)s2)c(S(=O)(=O)N2CCN(C)CC2)cc1OC

Standard InChI:  InChI=1S/C22H26ClN5O4S2/c1-27-8-10-28(11-9-27)34(29,30)20-14-19(32-3)18(31-2)12-15(20)13-21-25-26-22(33-21)24-17-6-4-16(23)5-7-17/h4-7,12,14H,8-11,13H2,1-3H3,(H,24,26)

Standard InChI Key:  WBLFGBPRPRMMDM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
   27.2583  -21.9163    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   28.0755  -21.9150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.6658  -21.2080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1334  -20.6898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1323  -21.5093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8403  -21.9183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5500  -21.5088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5471  -20.6862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8385  -20.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4242  -21.9173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7168  -21.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4256  -20.2813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4254  -19.4641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2596  -22.7335    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.2533  -20.2749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2321  -19.4540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8806  -18.9578    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   27.6081  -18.1874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7911  -18.2084    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.5588  -18.9919    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.0666  -17.5120    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.8837  -17.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2945  -18.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1056  -18.1937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5111  -17.4835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0884  -16.7772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2777  -16.7924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3282  -17.4752    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   26.5518  -23.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5511  -23.9559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2577  -24.3672    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.9666  -23.9587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9689  -23.1390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2559  -25.1844    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
 25 28  1  0
 14 29  1  0
 14 33  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 31 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2270952

   N-(4-chlorophenyl)-5-[[4,5-dimethoxy-2-(4-methylpiperazin-1-yl)sulfonylphenyl]methyl]-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: 524.07

Molecular Weight (Monoisotopic): 523.1115

AlogP: 3.48

#Rotatable Bonds: 8

Polar Surface Area: 96.89

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.45

CX Basic pKa: 5.99

CX LogP: 3.02

CX LogD: 3.00

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.48

Np Likeness Score: -1.83

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