5-Thiophen-2-yl-3-p-tolyl-[1,2,4]oxadiazole

ID: ALA191015

Cas Number: 330459-32-0

PubChem CID: 784811

Max Phase: Preclinical

Molecular Formula: C13H10N2OS

Molecular Weight: 242.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(-c2noc(-c3cccs3)n2)cc1

Standard InChI:  InChI=1S/C13H10N2OS/c1-9-4-6-10(7-5-9)12-14-13(16-15-12)11-3-2-8-17-11/h2-8H,1H3

Standard InChI Key:  ZBIZYSIIJRBDSE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 17 19  0  0  0  0  0  0  0  0999 V2000
    1.3250    1.7083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6542    1.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9917    1.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7375    0.4333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9125    0.4333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1250    1.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7958    0.9875    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.7750    1.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3833    2.2583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4625    1.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2083    2.2583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3875    0.9208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9417    2.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7250    2.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1667    1.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3417    1.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1292    2.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  3  2  0
  5  2  1  0
  6  2  1  0
  7  6  1  0
  8  3  1  0
  9  6  2  0
 10  7  1  0
 11  9  1  0
 12  8  2  0
 13  8  1  0
 14 13  2  0
 15 12  1  0
 16 14  1  0
 17 16  1  0
  5  4  1  0
 11 10  2  0
 15 16  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA191015

   5-Thiophen-2-yl-3-p-tolyl-[1,2,4]oxadiazole

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: 242.30

Molecular Weight (Monoisotopic): 242.0514

AlogP: 3.77

#Rotatable Bonds: 2

Polar Surface Area: 38.92

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.34

CX LogD: 4.34

Aromatic Rings: 3

Heavy Atoms: 17

QED Weighted: 0.69

Np Likeness Score: -2.44

References

1. Zhang HZ, Kasibhatla S, Kuemmerle J, Kemnitzer W, Ollis-Mason K, Qiu L, Crogan-Grundy C, Tseng B, Drewe J, Cai SX..  (2005)  Discovery and structure-activity relationship of 3-aryl-5-aryl-1,2,4-oxadiazoles as a new series of apoptosis inducers and potential anticancer agents.,  48  (16): [PMID:16078840] [10.1021/jm050292k]

2. PubChem BioAssay data set, 

3. PubChem BioAssay data set, 

4. Isabel, Elise E and 14 more authors.  2003-07-07  Nicotinyl aspartyl ketones as inhibitors of caspase-3.  [PMID:12798321]

5. Becker, Joseph W JW and 17 more authors.  2004-05-06  Reducing the peptidyl features of caspase-3 inhibitors: a structural analysis.  [PMID:15115390]

6. Mellon, Christophe C and 16 more authors.  2005-09-01  Lipophilic versus hydrogen-bonding effect in P3 on potency and selectivity of valine aspartyl ketones as caspase 3 inhibitors.  [PMID:16023344]

7. Chu, Wenhua W and 8 more authors.  2005-12-01  N-benzylisatin sulfonamide analogues as potent caspase-3 inhibitors: synthesis, in vitro activity, and molecular modeling studies.  [PMID:16302804]

8. Chen, Yi-Hua YH and 9 more authors.  2006-03-09  Design, synthesis, and biological evaluation of isoquinoline-1,3,4-trione derivatives as potent caspase-3 inhibitors.  [PMID:16509578]

9. Putt, Karson S KS and 12 more authors.  2006-10  Small-molecule activation of procaspase-3 to caspase-3 as a personalized anticancer strategy.  [PMID:16936720]

10. Isabel, Elise E and 17 more authors.  2007-03-15  Solid-phase analogue synthesis of caspase-3 inhibitors via palladium-catalyzed amination of 3-bromopyrazinones.  [PMID:17251019]

11. Chu, Wenhua W, Rothfuss, Justin J, Chu, Yunxiang Y, Zhou, Dong D and Mach, Robert H RH.  2009-04-23  Synthesis and in vitro evaluation of sulfonamide isatin Michael acceptors as small molecule inhibitors of caspase-6.  [PMID:19326941]

12. Lakshmi, P Jhansi PJ and 8 more authors.  2009-08-15  Design, synthesis, and discovery of novel non-peptide inhibitor of Caspase-3 using ligand based and structure based virtual screening approach.  [PMID:19631549]

13. Havran, Lisa M LM and 16 more authors.  2009-11-15  3,4-Dihydropyrimido(1,2-a)indol-10(2H)-ones as potent non-peptidic inhibitors of caspase-3.  [PMID:19836248]

14. Chu, Wenhua; Rothfuss, Justin; Zhou, Dong and Mach, Robert H.  2011-04-15  Synthesis and evaluation of isatin analogs as caspase-3 inhibitors: introduction of a hydrophilic group increases potency in a whole cell assay.  [PMID:21441025]

15. Maillard, Michel C MC and 17 more authors.  2011-10-01  Exploiting differences in caspase-2 and -3 S₂ subsites for selectivity: structure-based design, solid-phase synthesis and in vitro activity of novel substrate-based caspase-2 inhibitors.  [PMID:21903398]

16. Prime, Michael E ME and 29 more authors.  2012-02-09  Discovery and structure-activity relationship of potent and selective covalent inhibitors of transglutaminase 2 for Huntington's disease.  [PMID:22224594]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays