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Cas Database

115509-32-5

115509-32-5

Identification

  • Product Name:1,2-Cyclopentanediol,3-(6-amino-9H-purin-9-yl)-4-fluoro-5-(hydroxymethyl)-, (1R,2S,3S,4R,5R)-rel-

  • CAS Number: 115509-32-5

  • EINECS:

  • Molecular Weight:283.26

  • Molecular Formula: C11H14 F N5 O3

  • HS Code:

  • Mol File:115509-32-5.mol

Synonyms:1,2-Cyclopentanediol,3-(6-amino-9H-purin-9-yl)-4-fluoro-5-(hydroxymethyl)-, (1a,2a,3b,4b,5b)- (9CI); 1,2-Cyclopentanediol,3-(6-amino-9H-purin-9-yl)-4-fluoro-5-(hydroxymethyl)-, (1a,2a,3b,4b,5b)-(?à)-

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Relevant articles and documentsAll total 5 Articles be found

Design, Synthesis, and Anti-RNA Virus Activity of 6′-Fluorinated-Aristeromycin Analogues

Yoon, Ji-Seong,Kim, Gyudong,Jarhad, Dnyandev B.,Kim, Hong-Rae,Shin, Young-Sup,Qu, Shuhao,Sahu, Pramod K.,Kim, Hea Ok,Lee, Hyuk Woo,Wang, Su Bin,Kong, Yun Jeong,Chang, Tong-Shin,Ogando, Natacha S.,Kovacikova, Kristina,Snijder, Eric J.,Posthuma, Clara C.,Van Hemert, Martijn J.,Jeong, Lak Shin

, p. 6346 - 6362 (2019)

The 6′-fluorinated aristeromycins were designed as dual-target antiviral compounds aimed at inhibiting both the viral RNA-dependent RNA polymerase (RdRp) and the host cell S-adenosyl-l-homocysteine (SAH) hydrolase, which would indirectly target capping of viral RNA. The introduction of a fluorine at the 6′-position enhanced the inhibition of SAH hydrolase and the activity against RNA viruses. The adenosine and N6-methyladenosine analogues 2a-e showed potent inhibition against SAH hydrolase, while only the adenosine derivatives 2a-c exhibited potent antiviral activity against all tested RNA viruses such as Middle East respiratory syndrome-coronavirus (MERS-CoV), severe acute respiratory syndrome-coronavirus, chikungunya virus, and/or Zika virus. 6′,6′-Difluoroaristeromycin (2c) showed the strongest antiviral effect for MERS-CoV, with a ~2.5 log reduction in infectious progeny titer in viral load reduction assay. The phosphoramidate prodrug 3a also demonstrated potent broad-spectrum antiviral activity, possibly by inhibiting the viral RdRp. This study shows that 6′-fluorinated aristeromycins can serve as starting points for the development of broad-spectrum antiviral agents that target RNA viruses.

Asymmetric Synthesis of (-)-6′-β-Fluoro-aristeromycin via Stereoselective Electrophilic Fluorination

Kim, Gyudong,Yoon, Ji-Seong,Jarhad, Dnyandev B.,Shin, Young Sup,Majik, Mahesh S.,Mulamoottil, Varughese A.,Hou, Xiyan,Qu, Shuhao,Park, Jiyong,Baik, Mu-Hyun,Jeong, Lak Shin

, p. 5732 - 5735 (2017/11/10)

(-)-6′-β-Fluoro-aristeromycin (2), a potent inhibitor of S-adenosylhomocysteine (AdoHcy) hydrolase, has been synthesized via stereoselective electrophilic fluorination followed by a purine base build-up approach. Interestingly, purine base condensation using a cyclic sulfate resulted in a synthesis of (+)-5′-β-fluoro-isoaristeromycin (2a). Computational analysis indicates that the fluorine atom controlled the regioselectivity of the purine base substitution.

Chiral syntheses of 6′-β-fluoroaristeromycin, 6′-β-fluoro-5′-noraristeromycin and aristeromycin

Yin, Xue-Qiang,Schneller, Stewart W.

, p. 7535 - 7538 (2007/10/03)

Carbocyclic nucleosides substituted at the C-6′ position are receiving increasing attention. Chiral synthetic accessibility to the biologically promising 6′-β-fluoroaristeromycin is lacking. Its preparation and that of the 5′-nor analogue are described. A

Synthesis and Antiviral Evaluation of 6'-Substituted Aristeromycins: Potential Mechanism-Based Inhibitors of S-Adenosylhomocysteine Hydrolase

Madhavan, G. V. Bindu,McGee, Danny P. C.,Rydzewski, Robert M.,Boehme, Richard,Martin, John C.,Prisbe, Ernest J.

, p. 1798 - 1804 (2007/10/02)

New carboxylic adenosine analogues substituted at the 6'-position with fluorine, hydroxyl, methylene, of hydroxymethyl have been synthesized as potential mechanism-based inhibitors of S-adenosylhomocysteine (AdoHcy) hydrolase.The synthetic routes began wi

Purinyl or pyrimidinyl substituted hydroxycyclopentane compounds useful as antivirals

-

, (2008/06/13)

Novel 4-substituted-5-hydroxymethyl-1,2-cyclopentanediols or 1-cyclopentanol substituted at the 3-position by various heterocyclic groups are useful as antiviral agents.

Process route upstream and downstream products

Process route

[(3aS,4S,5S,6R,6aR)-6-(6-Amino-purin-9-yl)-5-fluoro-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl]-methanol

[(3aS,4S,5S,6R,6aR)-6-(6-Amino-purin-9-yl)-5-fluoro-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl]-methanol

(+/-)-6'β-fluoroaristeromycin
115509-32-5

(+/-)-6'β-fluoroaristeromycin

Conditions
Conditions Yield
With hydrogenchloride; at 70 ℃; for 0.25h;
91%
9-((3aS,4S,5S,6R,6aR)-6-(tert-butoxymethyl)-5-fluoro-2,2-dimethyltetrahydro-4H-cyclopenta[d][1,3]dioxol-4-yl)-6-chloro-9H-purine

9-((3aS,4S,5S,6R,6aR)-6-(tert-butoxymethyl)-5-fluoro-2,2-dimethyltetrahydro-4H-cyclopenta[d][1,3]dioxol-4-yl)-6-chloro-9H-purine

(1R,2S,3S,4S,5R)-3-(6-amino-9H-purin-9-yl)-4-fluoro-5-(hydroxymethyl)cyclopentane-1,2-diol
115509-32-5

(1R,2S,3S,4S,5R)-3-(6-amino-9H-purin-9-yl)-4-fluoro-5-(hydroxymethyl)cyclopentane-1,2-diol

Conditions
Conditions Yield
9-((3aS,4S,5S,6R,6aR)-6-(tert-butoxymethyl)-5-fluoro-2,2-dimethyltetrahydro-4H-cyclopenta[d][1,3]dioxol-4-yl)-6-chloro-9H-purine; With ammonia; In tert-butyl alcohol; at 120 ℃; for 15h;
With trifluoroacetic acid; In water; at 50 ℃; for 15h;
71%
9-((3aS,4S,5R,6R,6aR)-6-(tert-butoxymethyl)-5-fluoro-2,2-dimethyltetrahydro-4H-cyclopenta[d][1,3]dioxol-4-yl)-6-chloro-9H-purine

9-((3aS,4S,5R,6R,6aR)-6-(tert-butoxymethyl)-5-fluoro-2,2-dimethyltetrahydro-4H-cyclopenta[d][1,3]dioxol-4-yl)-6-chloro-9H-purine

6'-β-fluoroaristeromycin
115509-32-5

6'-β-fluoroaristeromycin

Conditions
Conditions Yield
9-((3aS,4S,5R,6R,6aR)-6-(tert-butoxymethyl)-5-fluoro-2,2-dimethyltetrahydro-4H-cyclopenta[d][1,3]dioxol-4-yl)-6-chloro-9H-purine; With ammonia; In tert-butyl alcohol; at 120 ℃; for 15h;
With trifluoroacetic acid; In water; at 50 ℃; for 15h;
43%
Multi-step reaction with 2 steps
1: ammonia / tert-butyl alcohol / 100 °C / Inert atmosphere; Autoclave
2: trifluoroacetic acid / water / 5 h / 20 - 50 °C / Inert atmosphere
With ammonia; trifluoroacetic acid; In water; tert-butyl alcohol;
(+/-)-(1α,2β,3α,4α,5β)-2-azido-3,4-(dimethylmethylenedioxy)-5-<(phenylmethoxy)methyl>-1-cyclopentanol
100021-16-7

(+/-)-(1α,2β,3α,4α,5β)-2-azido-3,4-(dimethylmethylenedioxy)-5-<(phenylmethoxy)methyl>-1-cyclopentanol

(+/-)-6'β-fluoroaristeromycin
115509-32-5

(+/-)-6'β-fluoroaristeromycin

Conditions
Conditions Yield
Multi-step reaction with 8 steps
1: pyridine / CH2Cl2 / 1 h / Ambient temperature
2: 5.14 g / tris(dimethylamino)sulfur (trimethylsilyl)difluoride / tetrahydrofuran / 14 h / Ambient temperature
3: 56 percent / hydrogen / Lindlar catalyst / methanol / 48 h / 760 Torr
4: 62 percent / triethylamine / butan-1-ol / 48 h / 105 °C
5: 78 percent / 12 h / Heating
6: 59 percent / ammonia / methanol / 12 h / 90 °C
7: 80 percent / cyclohexene / 20percent Pd(OH)2/C / ethanol / 48 h / Heating
8: 91 percent / 10percent HCl / 0.25 h / 70 °C
With pyridine; hydrogenchloride; tris(dimethylamino)sulfonium trimethylsilyldifluoride; ammonia; hydrogen; triethylamine; cyclohexene; palladium dihydroxide; Lindlar's catalyst; In tetrahydrofuran; methanol; ethanol; dichloromethane; butan-1-ol;
(+/-)-(1β,2α,3α,4β,5β)-2,3-(dimethylmethylenedioxy)-5-fluoro-4-<(phenylmethoxy)methyl>-1-cyclopentanamine

(+/-)-(1β,2α,3α,4β,5β)-2,3-(dimethylmethylenedioxy)-5-fluoro-4-<(phenylmethoxy)methyl>-1-cyclopentanamine

(+/-)-6'β-fluoroaristeromycin
115509-32-5

(+/-)-6'β-fluoroaristeromycin

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1: 62 percent / triethylamine / butan-1-ol / 48 h / 105 °C
2: 78 percent / 12 h / Heating
3: 59 percent / ammonia / methanol / 12 h / 90 °C
4: 80 percent / cyclohexene / 20percent Pd(OH)2/C / ethanol / 48 h / Heating
5: 91 percent / 10percent HCl / 0.25 h / 70 °C
With hydrogenchloride; ammonia; triethylamine; cyclohexene; palladium dihydroxide; In methanol; ethanol; butan-1-ol;
(+/-)-(1β,2α,3α,4β,5β)-2,3-(dimethylmethylenedioxy)-5-fluoro-4-<(phenylmethoxy)methyl>-1-cyclopentyl azide

(+/-)-(1β,2α,3α,4β,5β)-2,3-(dimethylmethylenedioxy)-5-fluoro-4-<(phenylmethoxy)methyl>-1-cyclopentyl azide

(+/-)-6'β-fluoroaristeromycin
115509-32-5

(+/-)-6'β-fluoroaristeromycin

Conditions
Conditions Yield
Multi-step reaction with 6 steps
1: 56 percent / hydrogen / Lindlar catalyst / methanol / 48 h / 760 Torr
2: 62 percent / triethylamine / butan-1-ol / 48 h / 105 °C
3: 78 percent / 12 h / Heating
4: 59 percent / ammonia / methanol / 12 h / 90 °C
5: 80 percent / cyclohexene / 20percent Pd(OH)2/C / ethanol / 48 h / Heating
6: 91 percent / 10percent HCl / 0.25 h / 70 °C
With hydrogenchloride; ammonia; hydrogen; triethylamine; cyclohexene; palladium dihydroxide; Lindlar's catalyst; In methanol; ethanol; butan-1-ol;
(+/-)-(1β,2α,3α,4β,5β)-1-<(5-amino-6-chloro-4-pyrimidinyl)amino>-2,3-(dimethylmethylenedioxy)-5-fluoro-4-<(phenylmethoxy)methyl>cyclopentane

(+/-)-(1β,2α,3α,4β,5β)-1-<(5-amino-6-chloro-4-pyrimidinyl)amino>-2,3-(dimethylmethylenedioxy)-5-fluoro-4-<(phenylmethoxy)methyl>cyclopentane

(+/-)-6'β-fluoroaristeromycin
115509-32-5

(+/-)-6'β-fluoroaristeromycin

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: 78 percent / 12 h / Heating
2: 59 percent / ammonia / methanol / 12 h / 90 °C
3: 80 percent / cyclohexene / 20percent Pd(OH)2/C / ethanol / 48 h / Heating
4: 91 percent / 10percent HCl / 0.25 h / 70 °C
With hydrogenchloride; ammonia; cyclohexene; palladium dihydroxide; In methanol; ethanol;
(+/-)-(1β,2α,3α,4β,5β)-1-(6-chloro-9H-purin-9-yl)-2,3-(dimethylmethylenedioxy)-5-fluoro-4-<(phenylmethoxy)methyl>cyclopentane

(+/-)-(1β,2α,3α,4β,5β)-1-(6-chloro-9H-purin-9-yl)-2,3-(dimethylmethylenedioxy)-5-fluoro-4-<(phenylmethoxy)methyl>cyclopentane

(+/-)-6'β-fluoroaristeromycin
115509-32-5

(+/-)-6'β-fluoroaristeromycin

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: 59 percent / ammonia / methanol / 12 h / 90 °C
2: 80 percent / cyclohexene / 20percent Pd(OH)2/C / ethanol / 48 h / Heating
3: 91 percent / 10percent HCl / 0.25 h / 70 °C
With hydrogenchloride; ammonia; cyclohexene; palladium dihydroxide; In methanol; ethanol;
(+/-)-(1β,2α,3α,4β,5β)-1-adenin-9-yl-2,3-(dimethylmethylenedioxy)-5-fluoro-4-<(phenylmethoxy)methyl>cyclopentane

(+/-)-(1β,2α,3α,4β,5β)-1-adenin-9-yl-2,3-(dimethylmethylenedioxy)-5-fluoro-4-<(phenylmethoxy)methyl>cyclopentane

(+/-)-6'β-fluoroaristeromycin
115509-32-5

(+/-)-6'β-fluoroaristeromycin

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 80 percent / cyclohexene / 20percent Pd(OH)2/C / ethanol / 48 h / Heating
2: 91 percent / 10percent HCl / 0.25 h / 70 °C
With hydrogenchloride; cyclohexene; palladium dihydroxide; In ethanol;
Trifluoro-methanesulfonic acid (3aS,4S,5S,6R,6aR)-4-azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-yl ester

Trifluoro-methanesulfonic acid (3aS,4S,5S,6R,6aR)-4-azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-yl ester

(+/-)-6'β-fluoroaristeromycin
115509-32-5

(+/-)-6'β-fluoroaristeromycin

Conditions
Conditions Yield
Multi-step reaction with 7 steps
1: 5.14 g / tris(dimethylamino)sulfur (trimethylsilyl)difluoride / tetrahydrofuran / 14 h / Ambient temperature
2: 56 percent / hydrogen / Lindlar catalyst / methanol / 48 h / 760 Torr
3: 62 percent / triethylamine / butan-1-ol / 48 h / 105 °C
4: 78 percent / 12 h / Heating
5: 59 percent / ammonia / methanol / 12 h / 90 °C
6: 80 percent / cyclohexene / 20percent Pd(OH)2/C / ethanol / 48 h / Heating
7: 91 percent / 10percent HCl / 0.25 h / 70 °C
With hydrogenchloride; tris(dimethylamino)sulfonium trimethylsilyldifluoride; ammonia; hydrogen; triethylamine; cyclohexene; palladium dihydroxide; Lindlar's catalyst; In tetrahydrofuran; methanol; ethanol; butan-1-ol;

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