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7-chloro-11-(4-methylpiperazin-1-yl)-dibenzo[b,f][1,4]oxazepine

ID: ALA213912

Cas Number: 3455-10-5

PubChem CID: 11846300

Max Phase: Preclinical

Molecular Formula: C18H18ClN3O

Molecular Weight: 327.82

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Synonyms: VUF-6884 | VUF-6884|CHEMBL213912|7-chloro-11-(4-methyl-piperazin-1-yl)-dibenzo[b,f][1,4]oxazepine|3455-10-5|BDBM50191289|PD129259|2-chloro-6-(4-methylpiperazin-1-yl)benzo[b][1,4]benzoxazepine|7-chloro-11-(4-methylpiperazin-1-yl)-dibenzo[b,f][1,4]oxazepine|7-chloro-11-(4-methylpiperazin-1-yl)dibenzo[b,f][1,4]oxazepine

Canonical SMILES:  CN1CCN(C2=Nc3ccc(Cl)cc3Oc3ccccc32)CC1

Standard InChI:  InChI=1S/C18H18ClN3O/c1-21-8-10-22(11-9-21)18-14-4-2-3-5-16(14)23-17-12-13(19)6-7-15(17)20-18/h2-7,12H,8-11H2,1H3

Standard InChI Key:  FSRSEANZUZHDHK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
    4.4024  -20.5402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4013  -21.3629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1120  -21.7733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1102  -20.1298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8207  -21.3620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8215  -20.5367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4700  -20.0167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4714  -21.8792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2806  -21.6922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2760  -20.1929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6369  -20.9423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4645  -21.0034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9323  -20.3158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5664  -19.5652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7398  -19.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7947  -22.3315    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4944  -23.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0047  -23.7318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8163  -23.6105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1151  -22.8455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6024  -22.2020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3279  -24.2517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6920  -20.1303    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
 10 11  2  0
  2  3  1  0
 11 12  1  0
  5  6  1  0
 12 13  2  0
  3  5  2  0
 13 14  1  0
  6  7  1  0
 14 15  2  0
 15 10  1  0
  1  2  2  0
  9 16  1  0
 16 17  1  0
  5  8  1  0
  7 10  1  0
  6  4  2  0
  8  9  2  0
  9 11  1  0
 16 21  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
  4  1  1  0
 19 22  1  0
  1 23  1  0
M  END

Associated Targets(Human)

HRH4 Tchem Histamine H4 receptor (3997 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HRH3 Tclin Histamine H3 receptor (10389 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HRH2 Tclin Histamine H2 receptor (5428 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HRH1 Tclin Histamine H1 receptor (7573 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HRH4 Tchem Histamine receptor (H3 and H4) (48 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

Calculated Properties

Molecular Weight: 327.82Molecular Weight (Monoisotopic): 327.1138AlogP: 3.77#Rotatable Bonds:
Polar Surface Area: 28.07Molecular Species: NEUTRALHBA: 4HBD:
#RO5 Violations: HBA (Lipinski): 4HBD (Lipinski): #RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: 7.23CX LogP: 3.46CX LogD: 3.24
Aromatic Rings: 2Heavy Atoms: 23QED Weighted: 0.74Np Likeness Score: -0.75

References

1. Smits RA, Lim HD, Stegink B, Bakker RA, de Esch IJ, Leurs R..  (2006)  Characterization of the histamine H4 receptor binding site. Part 1. Synthesis and pharmacological evaluation of dibenzodiazepine derivatives.,  49  (15): [PMID:16854056] [10.1021/jm051008s]
2. Smits RA, Lim HD, Hanzer A, Zuiderveld OP, Guaita E, Adami M, Coruzzi G, Leurs R, de Esch IJ..  (2008)  Fragment based design of new H4 receptor-ligands with anti-inflammatory properties in vivo.,  51  (8): [PMID:18357976] [10.1021/jm7014217]
3. Smits RA, de Esch IJ, Zuiderveld OP, Broeker J, Sansuk K, Guaita E, Coruzzi G, Adami M, Haaksma E, Leurs R..  (2008)  Discovery of quinazolines as histamine H4 receptor inverse agonists using a scaffold hopping approach.,  51  (24): [PMID:19053770] [10.1021/jm800876b]
4. Smits RA, Lim HD, van der Meer T, Kuhne S, Bessembinder K, Zuiderveld OP, Wijtmans M, de Esch IJ, Leurs R..  (2012)  Ligand based design of novel histamine H₄ receptor antagonists; fragment optimization and analysis of binding kinetics.,  22  (1): [PMID:22153663] [10.1016/j.bmcl.2011.10.104]
5. Hammer SG, Gobleder S, Naporra F, Wittmann HJ, Elz S, Heinrich MR, Strasser A..  (2016)  2,4-Diaminopyrimidines as dual ligands at the histamine H1 and H4 receptor-H1/H4-receptor selectivity.,  26  (2): [PMID:26718844] [10.1016/j.bmcl.2015.12.035]
6. Liu, C C and 10 more authors.  2001-03  Cloning and pharmacological characterization of a fourth histamine receptor (H(4)) expressed in bone marrow.  [PMID:11179434]
7. Nguyen, T T and 10 more authors.  2001-03  Discovery of a novel member of the histamine receptor family.  [PMID:11179435]
8. Zhu, Y Y and 18 more authors.  2001-03  Cloning, expression, and pharmacological characterization of a novel human histamine receptor.  [PMID:11179436]
9. Morse, K L KL and 17 more authors.  2001-03  Cloning and characterization of a novel human histamine receptor.  [PMID:11181941]
10. Thurmond, Robin L RL and 11 more authors.  2004-04  A potent and selective histamine H4 receptor antagonist with anti-inflammatory properties.  [PMID:14722321]
11. Lim, Herman D HD and 5 more authors.  2005-09  Evaluation of histamine H1-, H2-, and H3-receptor ligands at the human histamine H4 receptor: identification of 4-methylhistamine as the first potent and selective H4 receptor agonist.  [PMID:15947036]
12. Wijtmans, Maikel M and 16 more authors.  2008-05-22  4-benzyl-1H-imidazoles with oxazoline termini as histamine H3 receptor agonists.  [PMID:18433114]
13. Altenbach, Robert J RJ and 21 more authors.  2008-10-23  Structure-activity studies on a series of a 2-aminopyrimidine-containing histamine H4 receptor ligands.  [PMID:18811133]
14. Liu, Huaqing H and 18 more authors.  2008-11-27  cis-4-(Piperazin-1-yl)-5,6,7a,8,9,10,11,11a-octahydrobenzofuro[2,3-h]quinazolin-2-amine (A-987306), a new histamine H4R antagonist that blocks pain responses against carrageenan-induced hyperalgesia.  [PMID:18983139]
15. Smits, Rogier A RA and 9 more authors.  2008-12-25  Discovery of quinazolines as histamine H4 receptor inverse agonists using a scaffold hopping approach.  [PMID:19053770]
16. Smits, Rogier A RA and 9 more authors.  2010-03-25  Synthesis and QSAR of quinazoline sulfonamides as highly potent human histamine H4 receptor inverse agonists.  [PMID:20192225]
17. Igel, Patrick P, Dove, Stefan S and Buschauer, Armin A.  2010-12-15  Histamine H4 receptor agonists.  [PMID:21044842]
18. Verheij, Mark H P and 13 more authors.  2011-09-15  Fragment library screening reveals remarkable similarities between the G protein-coupled receptor histamine H₄ and the ion channel serotonin 5-HT₃A.  [PMID:21782429]
19. Savall, Brad M BM and 10 more authors.  2011-11-01  Tricyclic aminopyrimidine histamine H4 receptor antagonists.  [PMID:21920744]
20. Masood, M Abid MA and 14 more authors.  2011-11-01  Discovery of a series of potent and selective human H4 antagonists using ligand efficiency and libraries to explore structure-activity relationship (SAR).  [PMID:21955944]
21. Smits, Rogier A RA and 8 more authors.  2012-01-01  Ligand based design of novel histamine H₄ receptor antagonists; fragment optimization and analysis of binding kinetics.  [PMID:22153663]
22. Andaloussi, Mounir M and 7 more authors.  2013-05-01  A novel series of histamine H4 receptor antagonists based on the pyrido[3,2-d]pyrimidine scaffold: comparison of hERG binding and target residence time with PF-3893787.  [PMID:23558237]
23. Savall, Brad M BM and 8 more authors.  2014-03-27  Discovery and SAR of 6-alkyl-2,4-diaminopyrimidines as histamine H₄ receptor antagonists.  [PMID:24495018]
24. Tichenor, Mark S MS, Thurmond, Robin L RL, Venable, Jennifer D JD and Savall, Brad M BM.  2015-09-24  Functional Profiling of 2-Aminopyrimidine Histamine H4 Receptor Modulators.  [PMID:25993395]
25. Ko, Kwangseok K and 19 more authors.  2018-04-12  Discovery of a Novel Highly Selective Histamine H4 Receptor Antagonist for the Treatment of Atopic Dermatitis.  [PMID:29579390]
26. Malek, Rim and 21 more authors.  2019-12-26  New Dual Small Molecules for Alzheimer's Disease Therapy Combining Histamine H3 Receptor (H3R) Antagonism and Calcium Channels Blockade with Additional Cholinesterase Inhibition.  [PMID:31724859]
27. Corrêa, Michelle F and 11 more authors.  2021-01-15  Novel potent (dihydro)benzofuranyl piperazines as human histamine receptor ligands - Functional characterization and modeling studies on H3 and H4 receptors.  [PMID:33333448]

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