- Application of "hydrogen bonding interaction" in new drug development: Design, synthesis, antiviral activity, and sars of thiourea derivatives
-
A series of simple thiourea derivatives were designed based on the structure of natural product harmine and lead compound and synthesized from amines in one step. The antiviral activity of these thiourea derivatives was evaluated. Most of them exhibited significantly higher anti-TMV activity than commercial plant virucides ribavirin, harmine, and lead compound. The hydrogen bond was found to be important but not the more the better. The optimal compound (R,R)-20 showed the best anti-TMV activity in vitro and in vivo (in vitro activity, 75%/500 a??g/mL and 39%/100 a??g/mL; inactivation activity, 71%/500 a??g/mL and 35%/100 a??g/mL; curative activity, 73%/500 a??g/mL and 37%/100 a??g/mL; protection activity, 69%/500 a??g/mL and 33%/100 a??g/mL), which is significantly higher than that of Ningnanmycin. The systematic study provides strong evidence that these simple thiourea derivatives could become potential TMV inhibitors.
- Lu, Aidang,Wang, Ziwen,Zhou, Zhenghong,Chen, Jianxin,Wang, Qingmin
-
p. 1378 - 1384
(2015/03/05)
-
- Microwave assisted synthesis of 1,3,4-oxadiazole/thiohydantoin hybrid derivatives via dehydrative cycliztion of semicarbazide
-
A series of compounds containing both 1,3,4-oxadiazole and thiohydantoin were synthesized as a promising scaffold for application in medicinal chemistry. The key step of the synthesis is a microwave-assisted cyclization of semicarbazides possessing a thiohydantoin moiety at one of the acyl termini using POCl3 as a dehydrating reagent. A wide range of semicarbazides were prepared through the substitution of hydrazides with an N-acylated thiohydantoin derived from the cyclization of the corresponding isothiocyanate with an amino acid and subsequent N-acylation of the resultant thiohydrantion. Consequently, the 58 number of 1,3,4-oxadiazole derivatives having a thiohydantoin substituent were prepared in good overall yields. Thiohydantoin 134-Oxadiazole Semicarbazide Microwave Amino acid Acknowledgments. This research was conducted under the Industrial Infrastructure Program for Fundamental Technologies and Institute for Advancement of Technology through the Inter-ER Cooperation Projects (R0002016) which are funded by the Ministry of Trade, Industry & Energy, Korea to YDG and Open Translational Research Center for Innovative Drug (2012M3A9C1053532) which are funded by National Research Foundation of Korea.
- Yang, Seung-Ju,Lee, Jae-Min,Lee, Gee-Hyung,Kim, NaYeon,Kim, Yong-Sang,Gong, Young-Dae
-
supporting information
p. 3609 - 3617
(2015/02/05)
-
- "Cofactor"-controlled enantioselective catalysis
-
We report an achiral bisphosphine rhodium complex equipped with a binding site for the recognition of chiral anion guests. Upon binding small chiral guests-cofactors-the rhodium complex becomes chiral and can thus be used for asymmetric catalysis. Screening of a library of cofactors revealed that the best cofactors lead to hydrogenation catalysts that form the products with high enantioselectivity (ee?s up to 99%). Interestingly, a competition experiment shows that even in a mixture of 12 cofactors high ee is obtained, indicating that the complex based on the best cofactor dominates the catalysis.
- Dydio, Pawel,Rubay, Christophe,Gadzikwa, Tendai,Lutz, Martin,Reek, Joost N. H.
-
supporting information; experimental part
p. 17176 - 17179
(2011/12/13)
-
- The highly enantioselective Michael addition of ketones to nitrodienes catalyzed by the efficient organocatalyst system of pyrrolidinyl-thioimidazole and chiral thioureido acid
-
The highly enantioselective Michael addition reaction of ketones to nitrodienes was promoted efficiently by the accessible and fine-tunable organocatalytic system of pyrrolidinyl-thioimidazole and chiral thioureido acid. The corresponding adducts were afforded in good yields with high diastereoselectivities (up to 99:1) and excellent enantioselectivities (up to 99% ee). The Royal Society of Chemistry 2010.
- Li, Zhao-Bo,Luo, Shu-Ping,Guo, Yi,Xia, Ai-Bao,Xu, Dan-Qian
-
supporting information; experimental part
p. 2505 - 2508
(2010/08/07)
-
- A chiral thioureido acid as an effective additive for enantioselective organocatalytic Michael additions of nitroolefins
-
A novel and effective organocatalytic system consisting of pyrrolidinyl-thioimidazole and a chiral thioureido acid efficiently catalyzed the asymmetric Michael addition reactions of ketones to nitroolefins to afford the adducts with high diastereoselectivities (up to 99: 1) and excellent enantioselectivities (up to 99% ee). The Royal Society of Chemistry 2008.
- Xu, Dan-Qian,Yue, Hua-Dong,Luo, Shu-Ping,Xia, Ai-Bao,Zhang, Shuai,Xu, Zhen-Yuan
-
supporting information; experimental part
p. 2054 - 2057
(2009/02/01)
-
- Synthesis and Properties of N-Tritylthio Nucleoside Derivatives and Reductive Removal of the Tritylthio Group by Use of Tributyltin Hydride and Tris(trimethylsilyl)silane
-
N-Sulfenylations of ribo- and deoxyribo-nucleoside derivatives have been studied by the use of triphenylmethanesulfenyl chloride as a sulfenylating reagent under a variety of conditions.A two-phase system using 0.2 mol dm-3 Na2CO3-CH2Cl2 was found to be effective for N-sulfenylation of deoxycytidine, deoxyadenosine and guanosine derivatives (7b, 9b, 9c and 11d), which were partially or fully protected at the hydroxy functions.In the case of adenosine 9c, the N1-sulfenylated deoxyadenosine derivative 10f was also formed.For the N-sulfenylation of the 5'-protected thymidine derivative 7a, phase-transfer catalysis was successfully used.It was found that the N-TrS group could be removed by reductive C-S bond cleavage using Bu3SnH or (Me3Si)3SiH in toluene in the presence of AIBN under reflux for 5 min.In several cases, the Bu3SnH-mediated deprotection occurred in the absence of AIBN.When triethylborane or sonication was used as a radical initiator, the cleavage reaction could be carried out at room temperature.The stability of the TrS group attached to these nucleoside bases was examined under several acidic and basic conditions.
- Sekine, Mitsuo,Seio, Kohji
-
p. 3087 - 3094
(2007/10/02)
-