Helvetica Chimica Acta p. 554 - 564 (1991)
Update date:2022-08-05
Topics:
Seela, Frank
Muth, Heinz-Peter
Roeling, Angelika
The synthesis of 4-chloropyrrolo[2,3-d]pyrimidine a nd 2-amino-4- chloropyrrolo[2,3-d]pyrimidine α-D- and β-D-2′,3′- dideoxyribonucleosides 6a, b and 7a, b is described (Scheme 1). Glycosylation of the pyrrolo[2,3-d]-pyrimidinyl anions of 1a, b with in situ prepared 2,3-dideoxy-α /β-D-glycero-pentofuranosyl chloride (2) was regioselective but afforded anomeric mixtures of the 2′,3′- dideoxyribonucleosides 3a/4a and 3b/4b, respectively. The glycosylation products were deprotected and subjected to nucleophilic displacement yielding various pyrrolo[2,3-d]pyrimidine 2′,3′-deoxyribonucleosides related to 2′,3′-dideoxyadenosine and 2′,3′-dideoxyguanosine. One-pot phosphorylation gave the corresponding triphosphates. Some of them are strong inhibitors of HIV- 1 reverse trauscriptase, similar to corresponding purine 2′,3′-dideoxynucleotides, but exhibit a better selectivity index in comparison to DNA polymerases. According to that, the N(7) of the purine moiety is not an essential binding position of ddATP or ddGTP at the active centre of HIV-1 reverse transcriptase.
View MoreShandong Xiangde Biotechnology Co., Ltd
Contact:+86 -15066639877
Address:Sanba street
Anqing World Chemical Co., Ltd.
Contact:+86-556-5800026
Address:Daguan Economic Development Zone of circular economy industrial park Anqing City Anhui province
Shanghai Egoal Chemical Co.,Ltd
Contact:+86-21-50333091
Address:Yangming Garden Square 3,YangGao North Road 1188, Pudong New District, Shanghai
Anhui New Star Pharmaceutical Development Co., Ltd
Contact:013956922763
Address:Floor 3, F9A, F Workshop, No.110 Kexue Road, High-Tech Development Zone, Hefei, Anhui ,China
website:http://www.maisonchem.com.cn
Contact:0086-311-83833777
Address:Leitou industrial district, xinji, shijiazhuang city, hebei province,
Doi:10.1021/ol902959v
(2010)Doi:10.1016/j.molstruc.2011.10.038
(2011)Doi:10.1016/j.dyepig.2012.03.004
(2012)Doi:10.1055/s-0032-1316706
(2012)Doi:10.1016/j.molstruc.2011.10.013
(2011)Doi:10.1021/jm501111y
(2014)