2-(5-(6-bromobenzo[d][1,3]dioxol-5-yl)-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazol-1-yl)-4-(4-nitrophenyl)thiazole

ID: ALA3589312

PubChem CID: 122180785

Max Phase: Preclinical

Molecular Formula: C23H15BrN4O4S2

Molecular Weight: 555.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1ccc(-c2csc(N3N=C(c4cccs4)CC3c3cc4c(cc3Br)OCO4)n2)cc1

Standard InChI:  InChI=1S/C23H15BrN4O4S2/c24-16-9-21-20(31-12-32-21)8-15(16)19-10-17(22-2-1-7-33-22)26-27(19)23-25-18(11-34-23)13-3-5-14(6-4-13)28(29)30/h1-9,11,19H,10,12H2

Standard InChI Key:  LVSOEFZXQRFMPI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 39  0  0  0  0  0  0  0  0999 V2000
   -5.2259    3.2843    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7580    2.9756    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6168    1.4950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9669    0.8711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9730    1.9836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4652    1.8235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2867    0.5895    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7260    1.0120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7689    2.5114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3562    3.0155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6389    3.9757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1718    3.7645    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5265    5.1186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6150    6.1508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9329    5.4346    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.9490    5.3927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0025    4.3319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4525    4.7159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8448    6.1637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7872    7.2274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3372    6.8433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3560   -1.3452    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.2948    6.5510    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6071    7.7096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1424    5.7015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10  6  2  0
  5  6  1  0
 11 12  2  0
 12 13  1  0
 13 16  2  0
 15 14  2  0
 14 11  1  0
  3 11  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 15  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 20  1  0
  2 20  1  0
 22 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 12 31  1  0
 32 33  2  0
 32 34  1  0
 28 32  1  0
M  CHG  2  32   1  34  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3589312

   ---

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: 555.44

Molecular Weight (Monoisotopic): 553.9718

AlogP: 6.63

#Rotatable Bonds: 5

Polar Surface Area: 90.09

Molecular Species: NEUTRAL

HBA: 9

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 2.82

CX LogP: 7.04

CX LogD: 7.04

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.20

Np Likeness Score: -1.61

References

1. Shahavar Sulthana S, Arul Antony S, Balachandran C, Syed Shafi S..  (2015)  Thiophene and benzodioxole appended thiazolyl-pyrazoline compounds: Microwave assisted synthesis, antimicrobial and molecular docking studies.,  25  (14): [PMID:26028159] [10.1016/j.bmcl.2015.05.033]

Source

Source(1):

• Scientific Literature