calanolide a
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Synthesis ◽  
2019 ◽  
Vol 51 (19) ◽  
pp. 3617-3624 ◽  
Author(s):  
Ramil F. Fatykhov ◽  
Igor A. Khalymbadzha ◽  
Oleg N. Chupakhin ◽  
Valery N. Charushin ◽  
Anna K. Inyutina ◽  
...  

1-Nicotinoylbenzotriazole (NicBt) was uncovered as an efficient protecting agent for the site-selective acylation of resorcinol-type phenolic groups with almost equal reactivity. The use of NicBt allows selective protection of the 7-OH group in 5,7-dihydroxycoumarins in one simple scalable step, while combination of the nicotinoylation with tosylation–denicotinoylation or silylation–denicotinoylation yields 5-OH-protected 5,7-dihydroxycoumarins. Furthermore, nicotinoylated 5,7-dihydroxycoumarins proved useful in a gram-scale three-step preparation of a 2,2-dimethylpyrano[2,3-f]coumarin, a key intermediate for the synthesis of calanolide A, an HIV reverse transcriptase and Mycobacterium tuberculosis inhibitor, and its active analogues.


2017 ◽  
Vol 8 ◽  
Author(s):  
Xiangmeng Wu ◽  
Qinghao Zhang ◽  
Jiamei Guo ◽  
Yufei Jia ◽  
Ziqian Zhang ◽  
...  

2016 ◽  
Vol 9 ◽  
pp. S1597-S1602
Author(s):  
Anil U. Chopade ◽  
Manojkumar U. Chopade ◽  
Bhanu M. Chanda ◽  
Dilip D. Sawaikar ◽  
Kiran B. Sonawane ◽  
...  

2011 ◽  
Vol 56 (1) ◽  
pp. 341-351 ◽  
Author(s):  
Xiaofan Lu ◽  
Li Liu ◽  
Xu Zhang ◽  
Terrence Chi Kong Lau ◽  
Stephen Kwok Wing Tsui ◽  
...  

ABSTRACTNonnucleoside reverse transcriptase inhibitors (NNRTIs) are one of the key components of antiretroviral therapy drug regimen against human immunodeficiency virus type 1 (HIV-1) replication. We previously described a newly synthesized small molecule, 10-chloromethyl-11-demethyl-12-oxo-calanolide A (F18), a (+)-calanolide A analog, as a novel anti-HIV-1 NNRTI (H. Xue et al., J. Med. Chem. 53:1397–1401, 2010). Here, we further investigated its antiviral range, drug resistance profile, and underlying mechanism of action. F18 consistently displayed potent activity against primary HIV-1 isolates, including various subtypes of group M, circulating recombinant form (CRF) 01_AE, and laboratory-adapted drug-resistant viruses. Moreover, F18 displayed distinct profiles against 17 NNRTI-resistant pseudoviruses, with an excellent potency especially against one of the most prevalent strains with the Y181C mutation (50% effective concentration, 1.0 nM), which was in stark contrast to the extensively used NNRTIs nevirapine and efavirenz. Moreover, we induced F18-resistant viruses byin vitroserial passages and found that the mutation L100I appeared to be the dominant contributor to F18 resistance, further suggesting a binding motif different from that of nevirapine and efavirenz. F18 was nonantagonistic when used in combination with other antiretrovirals against both wild-type and drug-resistant viruses in infected peripheral blood mononuclear cells. Interestingly, F18 displayed a highly synergistic antiviral effect with nevirapine against nevirapine-resistant virus (Y181C). Furthermore,in silicodocking analysis suggested that F18 may bind to the HIV-1 reverse transcriptase differently from other NNRTIs. This study presents F18 as a new potential drug for clinical use and also presents a new mechanism-based design for future NNRTI.


ChemInform ◽  
2010 ◽  
Vol 25 (5) ◽  
pp. no-no
Author(s):  
B. CHENERA ◽  
M. L. WEST ◽  
J. A. FINKELSTEIN ◽  
G. B. DREYER

ChemInform ◽  
2010 ◽  
Vol 26 (2) ◽  
pp. no-no
Author(s):  
A. V. R. RAO ◽  
A. S. GAITONDE ◽  
K. R. C. PRAKASH ◽  
S. P. RAO
Keyword(s):  
Anti Hiv ◽  

ChemInform ◽  
2010 ◽  
Vol 26 (44) ◽  
pp. no-no
Author(s):  
A. KUCHERENKO ◽  
M. T. FLAVIN ◽  
W. A. BOULANGER ◽  
A. KHILEVICH ◽  
R. L. SHONE ◽  
...  
Keyword(s):  
Anti Hiv ◽  

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