129396-94-7Relevant academic research and scientific papers
Modifications of flexible nonyl chain and nucleobase head group of (+)-erythro-9-(2′s-hydroxy-3′s-nonyl)adenine [(+)-EHNA] as adenosine deaminase inhibitors
Kandalkar, Sachin R.,Ramaiah, Parimi Atchuta,Joshi, Manoj,Wavhal, Atul,Waman, Yogesh,Raje, Amol A.,Tambe, Ashwini,Ansari, Shariq,De, Siddhartha,Palle, Venkata P.,Mookhtiar, Kasim A.,Deshpande, Anil M.,Barawkar, Dinesh A.
, p. 5799 - 5819 (2017)
A series of terminal nonyl chain and nucleobase modified analogues of (+)-EHNA (III) were synthesized and evaluated for their ability to inhibit adenosine deaminase (ADA). The constrained carbon analogues of (+)-EHNA, 7a-7h, 10a-c, 12, 13, 14 and 17a-c appeared very potent with Ki values in the low nanomolar range. Thio-analogues of (+)-EHNA 24a-e wherein 5′C of nonyl chain replaced by sulfur atom found to be less potent compared to (+)-EHNA. Docking of the representative compounds into the active site of ADA was performed to understand structure-activity relationships. Compounds 7a (Ki: 1.1 nM) 7b (Ki: 5.2 nM) and 26a (Ki: 5.9 nM) showed suitable balance of potency, microsomal stability and demonstrated better pharmacokinetic properties as compared to (+)-EHNA and therefore may have therapeutic potential for various inflammatory diseases, hypertension and cancer.
A NEW SYNTHETIC APPROACH TO (+)-GALANTINIC ACID, DEGRADATION PRODUCT FROM THE PEPTIDE ANTIBIOTIC GALANTIN I, VIA 4-AMINO-3-HYDROXYPYRANOSE
Kano, Shinzo,Yokomatsu, Tsutomu,Shibuya, Shiroshi
, p. 13 - 16 (2007/10/02)
5-Phenylthiooxazolidin-2-ones, derived from L-serine, were subjected to photo-induced radical allylation to give the corresponding 4-substituted 4,5-trans-5-allyloxazolidin-2-ones. 4-Ethoxyethy derivative (13c) was led to N-Boc galantinic acid methyl ester via N-Boc 4-amino-3-hydroxypyranose.
