N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)benzamide

ID: ALA233000

Cas Number: 23903-48-2

PubChem CID: 290221

Max Phase: Preclinical

Molecular Formula: C16H14N2OS

Molecular Weight: 282.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1c(NC(=O)c2ccccc2)sc2c1CCCC2

Standard InChI:  InChI=1S/C16H14N2OS/c17-10-13-12-8-4-5-9-14(12)20-16(13)18-15(19)11-6-2-1-3-7-11/h1-3,6-7H,4-5,8-9H2,(H,18,19)

Standard InChI Key:  OKFHWMLGUMHKFC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
    6.7208   -7.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7208   -8.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4329   -8.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4329   -6.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1449   -7.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1494   -8.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9364   -8.2645    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.4183   -7.5935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9290   -6.9280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1796   -6.1420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4311   -5.3532    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2433   -7.5889    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6598   -8.3011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4847   -8.2965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2512   -9.0178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8978   -9.0111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7220   -9.0069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1314   -8.2896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7105   -7.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8876   -7.5828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
  9 10  1  0
  5  6  2  0
 10 11  3  0
  8 12  1  0
  1  2  1  0
 12 13  1  0
  1  4  1  0
 13 14  1  0
  2  3  1  0
 13 15  2  0
  3  6  1  0
 14 16  2  0
  6  7  1  0
 16 17  1  0
  7  8  1  0
 17 18  2  0
  8  9  2  0
 18 19  1  0
  9  5  1  0
 19 20  2  0
 20 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA233000

   N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)benzamide

Molecule Features

Natural Product: Yes

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: 282.37

Molecular Weight (Monoisotopic): 282.0827

AlogP: 3.75

#Rotatable Bonds: 2

Polar Surface Area: 52.89

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.45

CX LogD: 4.45

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.91

Np Likeness Score: -2.28

References

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2. Bamborough P, Drewry D, Harper G, Smith GK, Schneider K..  (2008)  Assessment of chemical coverage of kinome space and its implications for kinase drug discovery.,  51  (24): [PMID:19035792] [10.1021/jm8011036]

3. Amr Ael-G, Sherif MH, Assy MG, Al-Omar MA, Ragab I..  (2010)  Antiarrhythmic, serotonin antagonist and antianxiety activities of novel substituted thiophene derivatives synthesized from 2-amino-4,5,6,7-tetrahydro-N-phenylbenzo[b]thiophene-3-carboxamide.,  45  (12): [PMID:20950897] [10.1016/j.ejmech.2010.09.059]

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6. Szczepankiewicz, Bruce G BG and 25 more authors.  2006-06-15  Aminopyridine-based c-Jun N-terminal kinase inhibitors with cellular activity and minimal cross-kinase activity.  [PMID:16759099]

7. Zhao, Hongyu H and 19 more authors.  2006-07-27  Discovery of potent, highly selective, and orally bioavailable pyridine carboxamide c-Jun NH2-terminal kinase inhibitors.  [PMID:16854050]

8. Zarrinkar, Patrick P PP and 15 more authors.  2009-10-01  AC220 is a uniquely potent and selective inhibitor of FLT3 for the treatment of acute myeloid leukemia (AML).  [PMID:19654408]

9. Kamenecka, Ted and 13 more authors.  2010-01-14  Synthesis, biological evaluation, X-ray structure, and pharmacokinetics of aminopyrimidine c-jun-N-terminal kinase (JNK) inhibitors.  [PMID:19947601]

10. Goldstein, David M and 37 more authors.  2011-04-14  Discovery of 6-(2,4-difluorophenoxy)-2-[3-hydroxy-1-(2-hydroxyethyl)propylamino]-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one (pamapimod) and 6-(2,4-difluorophenoxy)-8-methyl-2-(tetrahydro-2H-pyran-4-ylamino)pyrido[2,3-d]pyrimidin-7(8H)-one (R1487) as orally bioavailable and highly selective inhibitors of p38α mitogen-activated protein kinase.  [PMID:21375264]

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12. Zhang, Tinghu and 17 more authors.  2012-01-27  Discovery of potent and selective covalent inhibitors of JNK.  [PMID:22284361]

13. Gong, Leyi L and 19 more authors.  2012-12-15  Discovery of a novel series of 4-quinolone JNK inhibitors.  [PMID:23142618]

14. Kusakabe, Ken-ichi K and 26 more authors.  2013-06-13  Indazole-based potent and cell-active Mps1 kinase inhibitors: rational design from pan-kinase inhibitor anthrapyrazolone (SP600125).  [PMID:23634759]

15. Li, Bei B and 14 more authors.  2013-09-15  Hit-to-lead optimization and kinase selectivity of imidazo[1,2-a]quinoxalin-4-amine derived JNK1 inhibitors.  [PMID:23916259]

16. He, Yuanjun and 9 more authors.  2014-01-01  Synthesis and SAR of novel isoxazoles as potent c-jun N-terminal kinase (JNK) inhibitors.  [PMID:24332487]

17. Patel, Snahel S and 26 more authors.  2015-01-08  Discovery of dual leucine zipper kinase (DLK, MAP3K12) inhibitors with activity in neurodegeneration models.  [PMID:25341110]

18. Koch, Pierre P, Gehringer, Matthias M and Laufer, Stefan A SA.  2015-01-08  Inhibitors of c-Jun N-terminal kinases: an update.  [PMID:25415535]

19. Patel, Snahel S and 19 more authors.  2015-10-22  Scaffold-Hopping and Structure-Based Discovery of Potent, Selective, And Brain Penetrant N-(1H-Pyrazol-3-yl)pyridin-2-amine Inhibitors of Dual Leucine Zipper Kinase (DLK, MAP3K12).  [PMID:26431428]

20. Simon-Szabó, Laura L and 14 more authors.  2016-01-15  Novel compounds reducing IRS-1 serine phosphorylation for treatment of diabetes.  [PMID:26704265]

21. Klaeger, Susan S and 47 more authors.  2017-12-01  The target landscape of clinical kinase drugs.  [PMID:29191878]

22. Schepetkin, Igor A and 11 more authors.  2019-01-01  Synthesis, biological evaluation, and molecular modeling of 11H-indeno[1,2-b]quinoxalin-11-one derivatives and tryptanthrin-6-oxime as c-Jun N-terminal kinase inhibitors.  [PMID:30347329]

23. Riggs, Jennifer R JR and 18 more authors.  2019-05-09  Design and Optimization Leading to an Orally Active TTK Protein Kinase Inhibitor with Robust Single Agent Efficacy.  [PMID:30998356]

24. Hatcher, John M and 8 more authors.  2020-11-12  Discovery of a Selective, Covalent IRAK1 Inhibitor with Antiproliferative Activity in MYD88 Mutated B-Cell Lymphoma.  [PMID:33214835]

Source

Source(1):

• Scientific Literature