1377273-10-3

Basic information

• Product Name: (1S,2R,3S,4R,5S)-4-(6-(3-chlorobenzylamino)-2-(pyren-4-ylethynyl)-9H-purin-9-yl)-2,3-dihydroxy-N-methylbicyclo[3.1.0]hexane-1-carboxamide
• CAS NO: 1377273-10-3
• Molecular Weight: 653.14
• Mol File: 1377273-10-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1S,2R,3S,4R,5S)-4-(6-(3-chlorobenzylamino)-2-(pyren-4-ylethynyl)-9H-purin-9-yl)-2,3-dihydroxy-N-methylbicyclo[3.1.0]hexane-1-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2R,3S,4R,5S)-4-(6-(3-chlorobenzylamino)-2-(pyren-4-ylethynyl)-9H-purin-9-yl)-2,3-dihydroxy-N-methylbicyclo[3.1.0]hexane-1-carboxamide(1377273-10-3)
• EPA Substance Registry System: (1S,2R,3S,4R,5S)-4-(6-(3-chlorobenzylamino)-2-(pyren-4-ylethynyl)-9H-purin-9-yl)-2,3-dihydroxy-N-methylbicyclo[3.1.0]hexane-1-carboxamide(1377273-10-3)

Safety Data

• Hazardous Substances Data: 1377273-10-3(Hazardous Substances Data)

Upstream product

• 4152-90-3 m-chlorobenzylamine 
• 1732-26-9 4-bromopyrene 
• 1388186-92-2 C₄₁H₃₃ClN₆O₃ 
• 600168-40-9 trimethyl(pyren-4-ylethynyl)silane 
• 793695-83-7 (1'S,2'R,3'S,4'R,5'S)-4'-[6-(3-chlorobenzylamino)-2-iodopurin-9-yl]-2',3'-isopropylidenebicyclo[3.1.0]hexane-1'-carboxylic acid ethyl ester 
• 185506-23-4 4-Ethynylpyrene 
• 793695-77-9 (1'S,2'R,3'S,4'R,5'S)-4'-[6-chloro-2-iodopurin-9-yl]-2',3'-isopropylidenebicyclo[3.1.0]hexane-1'-carboxylic acid ethyl ester 

Relevant articles and documents

Structure-guided design of A3 adenosine receptor-selective nucleosides: Combination of 2-arylethynyl and bicyclo[3.1.0]hexane substitutions

(N)-Methanocarba adenosine 5′-methyluronamides containing known A3 AR (adenosine receptor)-enhancing modifications, i.e., 2-(arylethynyl)adenine and N6-methyl or N6-(3-substituted- benzyl), were nanomolar full agonists of human (h) A3AR and highly selective (Ki ～0.6 nM, N6-methyl 2-(halophenylethynyl) analogues 13 and 14). Combined 2-arylethynyl-N6-3-chlorobenzyl substitutions preserved A3AR affinity/selectivity in the (N)-methanocarba series (e.g., 3,4-difluoro full agonist MRS5698 31, K i 3 nM, human and mouse A3) better than that for ribosides. Polyaromatic 2-ethynyl N6-3-chlorobenzyl analogues, such as potent linearly extended 2-p-biphenylethynyl MRS5679 34 (Ki hA3 3.1 nM; A1, A2A, inactive) and fluorescent 1-pyrene adduct MRS5704 35 (Ki hA3 68.3 nM), were conformationally rigid; receptor docking identified a large, mainly hydrophobic binding region. The vicinity of receptor-bound C2 groups was probed by homology modeling based on recent X-ray structure of an agonist-bound A2AAR, with a predicted helical rearrangement requiring an agonist-specific outward displacement of TM2 resembling opsin. Thus, the X-ray structure of related A2AAR is useful in guiding the design of new A3AR agonists.