2-Hydroxymethyl-5-{6-[2-(3,4,5-trimethoxy-phenyl)-ethylamino]-purin-9-yl}-tetrahydro-furan-3,4-diol

ID: ALA610812

PubChem CID: 46877206

Max Phase: Preclinical

Molecular Formula: C21H27N5O7

Molecular Weight: 461.48

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Bioactivity Summary Target Summary Assay Summary

Names and Identifiers

Canonical SMILES: COc1cc(CCNc2ncnc3c2ncn3C2O[C@H](CO)[C@@H](O)[C@H]2O)cc(OC)c1OC

Standard InChI: InChI=1S/C21H27N5O7/c1-30-12-6-11(7-13(31-2)18(12)32-3)4-5-22-19-15-20(24-9-23-19)26(10-25-15)21-17(29)16(28)14(8-27)33-21/h6-7,9-10,14,16-17,21,27-29H,4-5,8H2,1-3H3,(H,22,23,24)/t14-,16-,17-,21?/m1/s1

Standard InChI Key: JJOLJRMRMXFERM-BROWDQIMSA-N

Molfile:

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
    5.5167   -5.6042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5000   -6.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9417   -5.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9375   -4.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5125   -4.6292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3167   -7.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8667   -5.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0167   -6.6417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7167   -7.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5292   -6.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4167   -4.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4167   -5.7250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8125   -3.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9042   -4.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8167   -3.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3167   -2.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9000   -5.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8500   -3.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3417   -3.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8542   -3.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6792   -8.0667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4125   -3.9167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3500   -8.0667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2917   -2.7542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3042   -3.9542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3167   -2.1417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9542   -6.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8917   -3.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5125   -7.2042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3750   -3.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7750   -3.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3125   -4.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8000   -1.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  3  1  0
  5  7  2  0
  6  2  1  0
  7  1  1  0
  8  2  1  0
  9  6  1  0
 10  8  1  0
 11  4  2  0
 12  3  2  0
 13 15  1  0
 14 17  2  0
 15 19  2  0
 16 18  1  0
 17 12  1  0
 18 20  2  0
 19 20  1  0
 20 30  1  0
  6 21  1  6
 22 11  1  0
  9 23  1  6
 24 13  1  0
 25 15  1  0
 26 16  1  0
 10 27  1  1
 28 22  1  0
 29 27  1  0
 30 28  1  0
 31 24  1  0
 32 25  1  0
 33 26  1  0
  4  5  1  0
  9 10  1  0
 14 11  1  0
 16 13  2  0
M  END

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

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: 461.48	Molecular Weight (Monoisotopic): 461.1910	AlogP: 0.12	#Rotatable Bonds: 9
Polar Surface Area: 153.24	Molecular Species: NEUTRAL	HBA: 12	HBD: 4
#RO5 Violations: 1	HBA (Lipinski): 12	HBD (Lipinski): 4	#RO5 Violations (Lipinski): 1
CX Acidic pKa: 12.45	CX Basic pKa: 4.74	CX LogP: -0.25	CX LogD: -0.25
Aromatic Rings: 3	Heavy Atoms: 33	QED Weighted: 0.34	Np Likeness Score: 0.62

References

1. Kusachi S, Thompson RD, Yamada N, Daly DT, Olsson RA.. (1986) Dog coronary artery adenosine receptor: structure of the N6-aryl subregion., 29 (6): [PMID:3012086] [10.1021/jm00156a016]
2. Hayallah, Alaa M AM and 7 more authors. 2002-03-28 1,8-disubstituted xanthine derivatives: synthesis of potent A2B-selective adenosine receptor antagonists. [PMID:11906291]
3. Saki, Mayumi M, Tsumuki, Hiroshi H, Nonaka, Hiromi H, Shimada, Junichi J and Ichimura, Michio M. 2002-05-31 KF26777 (2-(4-bromophenyl)-7,8-dihydro-4-propyl-1H-imidazo[2,1-i]purin-5(4H)-one dihydrochloride), a new potent and selective adenosine A3 receptor antagonist. [PMID:12063073]
4. Yan, Luo L, Burbiel, Joachim C JC, Maass, Astrid A and Müller, Christa E CE. 2003-11 Adenosine receptor agonists: from basic medicinal chemistry to clinical development. [PMID:14662005]
5. Kase, Hiroshi H and 27 more authors. 2003-12-09 Progress in pursuit of therapeutic A2A antagonists: the adenosine A2A receptor selective antagonist KW6002: research and development toward a novel nondopaminergic therapy for Parkinson's disease. [PMID:14663020]
6. Vu, Chi B CB and 14 more authors. 2004-08-12 Piperazine derivatives of [1,2,4]triazolo[1,5-a][1,3,5]triazine as potent and selective adenosine A2a receptor antagonists. [PMID:15294001]
7. Jacobson, Kenneth A KA and Gao, Zhan-Guo ZG. 2006-03 Adenosine receptors as therapeutic targets. [PMID:16518376]
8. Vu, Chi B CB and 10 more authors. 2006-11-30 Tricyclic imidazoline derivatives as potent and selective adenosine A1 receptor antagonists. [PMID:17125265]
9. Kalk, P P and 9 more authors. 2007-08 The adenosine A1 receptor antagonist SLV320 reduces myocardial fibrosis in rats with 5/6 nephrectomy without affecting blood pressure. [PMID:17558436]
10. Kuno, Atsushi A and 9 more authors. 2007-09 Protein kinase C protects preconditioned rabbit hearts by increasing sensitivity of adenosine A2b-dependent signaling during early reperfusion. [PMID:17632123]
11. Elzein, Elfatih E and Zablocki, Jeff J. 2008-12 A1 adenosine receptor agonists and their potential therapeutic applications. [PMID:19012505]
12. Gillespie, Roger J RJ and 6 more authors. 2009-05-15 Antagonists of the human A(2A) receptor. Part 5: Highly bio-available pyrimidine-4-carboxamides. [PMID:19362836]
13. Bedford, Simon T ST and 20 more authors. 2009-10-15 Discovery and optimization of potent and selective functional antagonists of the human adenosine A2B receptor. [PMID:19733067]
14. Fredholm, Bertil B BB, IJzerman, Adriaan P AP, Jacobson, Kenneth A KA, Linden, Joel J and Müller, Christa E CE. 2011-03 International Union of Basic and Clinical Pharmacology. LXXXI. Nomenclature and classification of adenosine receptors--an update. [PMID:21303899]
15. Baraldi, Pier Giovanni PG and 8 more authors. 2012-01-15 Pyrrolo- and pyrazolo-[3,4-e][1,2,4]triazolo[1,5-c]pyrimidines as adenosine receptor antagonists. [PMID:22204739]
16. Congreve, Miles and 11 more authors. 2012-03-08 Discovery of 1,2,4-triazine derivatives as adenosine A(2A) antagonists using structure based drug design. [PMID:22220592]
17. Inamdar, Gajanan S GS and 8 more authors. 2013-05 New insight into adenosine receptors selectivity derived from a novel series of [5-substituted-4-phenyl-1,3-thiazol-2-yl] benzamides and furamides. [PMID:23685887]
18. Gràcia, Jordi J and 20 more authors. 2016-12-08 Biphenyl Pyridazinone Derivatives as Inhaled PDE4 Inhibitors: Structural Biology and Structure-Activity Relationships. [PMID:27933955]
19. Basu, Sujay and 25 more authors. 2017-01-26 Design, Synthesis of Novel, Potent, Selective, Orally Bioavailable Adenosine A2A Receptor Antagonists and Their Biological Evaluation. [PMID:28055204]
20. Basu, Sujay S and 26 more authors. 2017-07-07 Design and synthesis of novel xanthine derivatives as potent and selective A2B adenosine receptor antagonists for the treatment of chronic inflammatory airway diseases. [PMID:28415011]
21. Paz, Odailson Santos OS, de Jesus Pinheiro, Milena M, do Espirito Santo, Renan Fernandes RF, Villarreal, Cristiane Flora CF and Castilho, Marcelo Santos MS. 2017-08-18 Nanomolar anti-sickling compounds identified by ligand-based pharmacophore approach. [PMID:28528302]
22. Aurelio, Luigi and 10 more authors. 2018-03-08 A Structure-Activity Relationship Study of Bitopic N6-Substituted Adenosine Derivatives as Biased Adenosine A1 Receptor Agonists. [PMID:29446948]
23. Härter, Michael M and 8 more authors. 2019-02-01 Novel non-xanthine antagonist of the A2B adenosine receptor: From HTS hit to lead structure. [PMID:30576906]
24. Abdelrahman, Aliaa and 6 more authors. 2020-01-15 Substituted 4-phenylthiazoles: Development of potent and selective A1, A3 and dual A1/A3 adenosine receptor antagonists. [PMID:31780082]

2-Hydroxymethyl-5-{6-[2-(3,4,5-trimethoxy-phenyl)-ethylamino]-purin-9-yl}-tetrahydro-furan-3,4-diol

Names and Identifiers

Alternative Forms

Associated Targets(Human)

Molecule Features

Drug Indications

Mechanisms of Action

Calculated Properties

References

Source