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(1S,2R)-cis-2-(4-chlorobenzylamino)methyl-1-(1H-imidazol-4-yl)cyclopropane

ID: ALA376954

PubChem CID: 16082852

Max Phase: Preclinical

Molecular Formula: C14H16ClN3

Molecular Weight: 261.76

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  Clc1ccc(CNC[C@@H]2C[C@@H]2c2c[nH]cn2)cc1

Standard InChI:  InChI=1S/C14H16ClN3/c15-12-3-1-10(2-4-12)6-16-7-11-5-13(11)14-8-17-9-18-14/h1-4,8-9,11,13,16H,5-7H2,(H,17,18)/t11-,13-/m0/s1

Standard InChI Key:  QGRLYCYTQSXMLL-AAEUAGOBSA-N

Molfile:  

     RDKit          2D

 18 20  0  0  1  0  0  0  0  0999 V2000
    4.0167   -2.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8417   -2.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4292   -1.4796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3024   -2.6087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5559   -2.6087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5462   -2.2759    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9937   -2.8899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4083   -3.6045    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2156   -3.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2706   -2.1965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9849   -2.6094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6995   -2.1973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4123   -2.6120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1265   -2.2005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1274   -1.3746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4081   -0.9619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6968   -1.3758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8415   -0.9616    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  5 10  1  0
  1  4  1  1
 10 11  1  0
  3  2  1  0
 11 12  1  0
  2  5  1  1
 12 13  2  0
  6  7  2  0
 13 14  1  0
  1  3  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 15 18  1  0
  4  6  1  0
  7  8  1  0
  8  9  1  0
  9  4  2  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
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: 261.76Molecular Weight (Monoisotopic): 261.1033AlogP: 2.96#Rotatable Bonds: 5
Polar Surface Area: 40.71Molecular Species: BASEHBA: 2HBD: 2
#RO5 Violations: HBA (Lipinski): 3HBD (Lipinski): 2#RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: 9.47CX LogP: 2.35CX LogD: 0.26
Aromatic Rings: 2Heavy Atoms: 18QED Weighted: 0.87Np Likeness Score: -0.50

References

1. Watanabe M, Kazuta Y, Hayashi H, Yamada S, Matsuda A, Shuto S..  (2006)  Stereochemical diversity-oriented conformational restriction strategy. Development of potent histamine H3 and/or H4 receptor antagonists with an imidazolylcyclopropane structure.,  49  (18): [PMID:16942032] [10.1021/jm0603318]
2. 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]
3. Nguyen, T T and 10 more authors.  2001-03  Discovery of a novel member of the histamine receptor family.  [PMID:11179435]
4. Zhu, Y Y and 18 more authors.  2001-03  Cloning, expression, and pharmacological characterization of a novel human histamine receptor.  [PMID:11179436]
5. Morse, K L KL and 17 more authors.  2001-03  Cloning and characterization of a novel human histamine receptor.  [PMID:11181941]
6. Thurmond, Robin L RL and 11 more authors.  2004-04  A potent and selective histamine H4 receptor antagonist with anti-inflammatory properties.  [PMID:14722321]
7. 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]
8. Wijtmans, Maikel M and 16 more authors.  2008-05-22  4-benzyl-1H-imidazoles with oxazoline termini as histamine H3 receptor agonists.  [PMID:18433114]
9. 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]
10. 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]
11. 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]
12. 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]
13. Igel, Patrick P, Dove, Stefan S and Buschauer, Armin A.  2010-12-15  Histamine H4 receptor agonists.  [PMID:21044842]
14. 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]
15. Savall, Brad M BM and 10 more authors.  2011-11-01  Tricyclic aminopyrimidine histamine H4 receptor antagonists.  [PMID:21920744]
16. 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]
17. 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]
18. 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]
19. 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]
20. 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]
21. 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]
22. 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]
23. 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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