3-Amino-4-(4-phenyl-1,4-diazepan-1-yl)thieno[2,3-b]pyridine-2-carboxamide

ID: ALA2348339

PubChem CID: 69364461

Max Phase: Preclinical

Molecular Formula: C19H21N5OS

Molecular Weight: 367.48

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  NC(=O)c1sc2nccc(N3CCCN(c4ccccc4)CC3)c2c1N

Standard InChI:  InChI=1S/C19H21N5OS/c20-16-15-14(7-8-22-19(15)26-17(16)18(21)25)24-10-4-9-23(11-12-24)13-5-2-1-3-6-13/h1-3,5-8H,4,9-12,20H2,(H2,21,25)

Standard InChI Key:  DEXAFBASLBZBIA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   30.5690  -11.6470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5678  -12.4665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2759  -12.8755    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.2741  -11.2381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9827  -11.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9830  -12.4666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7659  -12.7208    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   33.2496  -12.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7655  -11.3889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0668  -12.0543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4757  -12.7619    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.4752  -11.3465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.0178  -10.6116    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.2716  -10.4210    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.5380  -10.0711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3516   -9.2735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0080  -10.0642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8546   -8.6310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1859   -9.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6707   -8.6296    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.0215   -7.8957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8374   -7.8320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1883   -7.0948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7246   -6.4209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9060   -6.4889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5587   -7.2263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  9 13  1  0
  4 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 16 18  1  0
 17 19  1  0
 18 20  1  0
 19 20  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
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 26 21  1  0
 20 21  1  0
M  END

Associated Targets(Human)

CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CDK19 Tchem Cell division cycle 2-like protein kinase 6 (553 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CDK8 Tchem Cell division protein kinase 8 (1536 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CDK8 Tchem Cyclin-dependent kinase 8/19 (99 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Rattus norvegicus (775804 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Liver microsomes (8692 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Cdk8 CDK8/CDK19 (27 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 367.48Molecular Weight (Monoisotopic): 367.1467AlogP: 2.69#Rotatable Bonds: 3
Polar Surface Area: 88.48Molecular Species: NEUTRALHBA: 6HBD: 2
#RO5 Violations: HBA (Lipinski): 6HBD (Lipinski): 4#RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: 4.70CX LogP: 2.71CX LogD: 2.71
Aromatic Rings: 3Heavy Atoms: 26QED Weighted: 0.74Np Likeness Score: -1.66

References

1. Saito K, Nakao A, Shinozuka T, Shimada K, Matsui S, Oizumi K, Yano K, Ohata K, Nakai D, Nagai Y, Naito S..  (2013)  Discovery and structure-activity relationship of thienopyridine derivatives as bone anabolic agents.,  21  (7): [PMID:23453217] [10.1016/j.bmc.2013.01.071]
2. Saito K, Shinozuka T, Nakao A, Kiho T, Kunikata T, Shiiki T, Nagai Y, Naito S..  (2019)  Synthesis and structure-activity relationship of 4-alkoxy-thieno[2,3-b]pyridine derivatives as potent alkaline phosphatase enhancers for osteoporosis treatment.,  29  (14): [PMID:31101474] [10.1016/j.bmcl.2019.05.014]
3.  (2019)  Compounds for treatment of hypoproliferative disorders, 
4.  (2020)  3-amino-4-(4-(4 (dimethylcarbamoyl) phenyl)-1,4-diazepan-1-yl) thieno [2,3-b] pyridine-2-carboxamide for use in cancer therapy and formulations comprising the same, 
5. Saito K, Shinozuka T, Nakao A, Kunikata T, Nakai D, Nagai Y, Naito S..  (2021)  Discovery of 3-amino-4-{(3S)-3-[(2-ethoxyethoxy)methyl]piperidin-1-yl}thieno[2,3-b]pyridine-2-carboxamide (DS96432529): A potent and orally active bone anabolic agent.,  54  [PMID:34742889] [10.1016/j.bmcl.2021.128440]