3-(6-Amino-purin-9-yl)-nonan-2-ol

ID: ALA296435

Chembl Id: CHEMBL296435

Cas Number: 79813-69-7

PubChem CID: 149790

Max Phase: Preclinical

Molecular Formula: C14H23N5O

Molecular Weight: 277.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCC[C@H]([C@H](C)O)n1cnc2c(N)ncnc21

Standard InChI:  InChI=1S/C14H23N5O/c1-3-4-5-6-7-11(10(2)20)19-9-18-12-13(15)16-8-17-14(12)19/h8-11,20H,3-7H2,1-2H3,(H2,15,16,17)/t10-,11+/m0/s1

Standard InChI Key:  IOSAAWHGJUZBOG-WDEREUQCSA-N

Alternative Forms

1. Parent:

   

   ALA296435

   (+)-EHNA

2. Alternative Forms:

   

   ALA296435

   EHNA hydrochloride

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: 277.37

Molecular Weight (Monoisotopic): 277.1903

AlogP: 2.30

#Rotatable Bonds: 7

Polar Surface Area: 89.85

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.70

CX LogP: 2.14

CX LogD: 2.14

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.76

Np Likeness Score: 0.00

References

1. Bastian G, Bessodes M, Panzica RP, Abushanab E, Chen SF, Stoeckler JD, Parks RE..  (1981)  Adenosine deaminase inhibitors. Conversion of a single chiral synthon into erythro- and threo-9-(2-hydroxy-3-nonyl)adenines.,  24  (12): [PMID:7310814] [10.1021/jm00144a002]

2. Curtis MA, Varkhedkar V, Pragnacharyulu PV, Abushanab E..  (1998)  Adenosine deaminase inhibitors. Synthesis and biological evaluation of aralkyladenines (ARADS).,  8  (13): [PMID:9873405] [10.1016/s0960-894x(98)00291-1]

3. Pragnacharyulu PV, Lu P, Abushanab E.  (1996)  Adenosine deaminase inhibitors. Synthesis and biological evaluation of chain modified analogs of (+)-EHNA,  6  (20): [10.1016/0960-894X(96)00439-8]

4. Vargeese C, Sarma MS, Pragnacharyulu PV, Abushanab E, Li SY, Stoeckler JD..  (1994)  Adenosine deaminase inhibitors. Synthesis and biological evaluation of putative metabolites of (+)-erythro-9-(2S-hydroxy-3R-nonyl)adenine.,  37  (22): [PMID:7966142] [10.1021/jm00048a020]

5. Zhao YZ, van Breemen RB, Nikolic D, Huang CR, Woodbury CP, Schilling A, Venton DL..  (1997)  Screening solution-phase combinatorial libraries using pulsed ultrafiltration/electrospray mass spectrometry.,  40  (25): [PMID:9406591] [10.1021/jm960729b]

6. Harriman GC, Poirot AF, Abushanab E, Midgett RM, Stoeckler JD..  (1992)  Adenosine deaminase inhibitors. Synthesis and biological evaluation of C1' and nor-C1' derivatives of (+)-erythro-9-(2(S)-hydroxy-3(R)-nonyl)adenine.,  35  (22): [PMID:1433220] [10.1021/jm00100a025]

7. Pragnacharyulu PV, Varkhedkar V, Curtis MA, Chang IF, Abushanab E..  (2000)  Adenosine deaminase inhibitors: synthesis and biological evaluation of unsaturated, aromatic, and oxo derivatives of (+)-erythro-9-(2'S-hydroxy-3'R-nonyl)adenine [(+)-EHNA].,  43  (24): [PMID:11101360] [10.1021/jm0002533]

8. Da Settimo F, Primofiore G, La Motta C, Taliani S, Simorini F, Marini AM, Mugnaini L, Lavecchia A, Novellino E, Tuscano D, Martini C..  (2005)  Novel, highly potent adenosine deaminase inhibitors containing the pyrazolo[3,4-d]pyrimidine ring system. Synthesis, structure-activity relationships, and molecular modeling studies.,  48  (16): [PMID:16078836] [10.1021/jm050136d]

9. Chambers RJ, Abrams K, Garceau NY, Kamath AV, Manley CM, Lilley SC, Otte DA, Scott DO, Sheils AL, Tess DA, Vellekoop AS, Zhang Y, Lam KT..  (2006)  A new chemical tool for exploring the physiological function of the PDE2 isozyme.,  16  (2): [PMID:16275071] [10.1016/j.bmcl.2005.10.005]

10. La Motta C, Sartini S, Mugnaini L, Salerno S, Simorini F, Taliani S, Marini AM, Da Settimo F, Lavecchia A, Novellino E, Antonioli L, Fornai M, Blandizzi C, Del Tacca M..  (2009)  Exploiting the pyrazolo[3,4-d]pyrimidin-4-one ring system as a useful template to obtain potent adenosine deaminase inhibitors.,  52  (6): [PMID:19226143] [10.1021/jm801427r]

11. Umar T, Hoda N.  (2015)  Selective inhibitors of phosphodiesterases: therapeutic promise for neurodegenerative disorders,  6  (12): [10.1039/C5MD00419E]

12. Kandalkar SR, Ramaiah PA, Joshi M, Wavhal A, Waman Y, Raje AA, Tambe A, Ansari S, De S, Palle VP, Mookhtiar KA, Deshpande AM, Barawkar DA..  (2017)  Modifications of flexible nonyl chain and nucleobase head group of (+)-erythro-9-(2's-hydroxy-3's-nonyl)adenine [(+)-EHNA] as adenosine deaminase inhibitors.,  25  (20): [PMID:28951094] [10.1016/j.bmc.2017.09.015]

13. Qiu X, Huang Y, Wu D, Mao F, Zhu J, Yan W, Luo HB, Li J..  (2018)  Discovery of novel purine nucleoside derivatives as phosphodiesterase 2 (PDE2) inhibitors: Structure-based virtual screening, optimization and biological evaluation.,  26  (1): [PMID:29174506] [10.1016/j.bmc.2017.11.022]

14. Huang XF, Cao YJ, Zhen J, Zhang DW, Kong R, Jiang WT, Xu Y, Song GQ, Ke HM, Liu L..  (2019)  Design, synthesis of novel purin-6-one derivatives as phosphodiesterase 2 (PDE2) inhibitors: The neuroprotective and anxiolytic-like effects.,  29  (3): [PMID:30554955] [10.1016/j.bmcl.2018.12.018]

15. Ručilová V,Świerczek A,Vanda D,Funk P,Lemrová B,Gawalska A,Bucki A,Nowak B,Zadrożna M,Pociecha K,Soural M,Wyska E,Pawłowski M,Chłoń-Rzepa G,Zajdel P.  (2021)  New imidazopyridines with phosphodiesterase 4 and 7 inhibitory activity and their efficacy in animal models of inflammatory and autoimmune diseases.,  209  [PMID:33022582] [10.1016/j.ejmech.2020.112854]

16. Hou R, He Y, Yan G, Hou S, Xie Z, Liao C..  (2021)  Zinc enzymes in medicinal chemistry.,  226  [PMID:34624823] [10.1016/j.ejmech.2021.113877]

Source

Source(1):

• Scientific Literature