Divergent synthesis of new α-glucosidase inhibitors obtained through a vinyl Grignard-mediated carbocyclisation
Literature Information
Ida M. B. Knudsen, Christinne Hedberg, Daisuke Ide, Anne Brinkø, Espen Z. Eikeland, Atsushi Kato, Henrik H. Jensen
Four new α-glucosidase inhibitors have been synthesised through 5–8 synthetic steps from a common synthetic intermediate obtained through a recently developed carbocyclisation. The compounds were designed as hybrids of the known glucosidase inhibitors valienamine, voglibose and miglitol. All four compounds showed activity against rat intestinal sucrase with the most potent inhibitor acting at low micromolar concentration. The newly synthesised compounds were not as potent as miglitol against sucrase but showed greater selectivity towards the tested glycosidases. The most potent inhibitors were docked into a homology model built for this study of rat intestinal sucrase explaining the difference in potency between two diastereoisomers with varying orientation of a secondary amine.
Recommended Journals
Related Literature
HFIP-promoted Michael reactions: direct para-selective C–H activation of anilines with maleimides
Bang Li, Qi Mao, Jia Zhou, Feng Liu, Na Ye
DOI: 10.1039/C8OB03073A
Expeditious access of chromone analogues via a Michael addition-driven multicomponent reaction
Liu-Jun He, Ya-Fei Luo, Dian-Yong Tang, Wei Yan, Hui-Kuan Lin, Hong-yu Li, Zhong-Zhu Chen, Zhi-Gang Xu
DOI: 10.1039/D0QO00145G
Synthesis and biological evaluation of fluorinated analogues of ripostatin A
Vladyslav Shenderman
DOI: 10.1039/C8OB02890G
Scalable electrochemical oxidant-and metal-free dehydrogenative coupling of S–H/N–H
Shanyu Tang, Yan Liu, Longjia Li, Xuanhe Ren, Jiao Li, Guanyu Yang, Heng Li, Bingxin Yuan
DOI: 10.1039/C8OB03211D
Hydroaminoalkylation of sterically hindered alkenes with N,N-dimethyl anilines using a scandium catalyst
Jianhong Su, Yiqun Zhou, Xin Xu
DOI: 10.1039/C8OB02657B
Synthesis of diphenylamine macrocycles and their anti-inflammatory effects
Alejandra Chávez-Riveros, Eduardo Hernández-Vázquez, Antonio Nieto-Camacho, Teresa Ramírez-Apan, Luis D. Miranda
DOI: 10.1039/C8OB03121E
Recent developments in palladium-catalyzed C–S bond formation
Jianxiao Li, Shaorong Yang, Wanqing Wu, Huanfeng Jiang
DOI: 10.1039/D0QO00377H
One-pot stapling of interchain disulfides of antibodies using an isobutylene motif
Shuang Sun, Padma Akkapeddi, Nuria Martínez-Sáez, Vukosava M. Torres, Carlos Cordeiro, Omar Boutureira
DOI: 10.1039/C8OB02877J
Imidazole carbamate probes for affinity guided azide-transfer to metal-binding proteins
Johan Palmfeldt
DOI: 10.1039/C8OB03017K
Mechanism and origins of stereo- and enantioselectivities of palladium-catalyzed hydroamination of racemic internal allenes via dynamic kinetic resolution: a computational study
Zhenzhen Wu, Mei Zhang, Yu Shi, Genping Huang
DOI: 10.1039/D0QO00174K
You might also like
What industries use (1R,3S)-1,3-Cyclopentanediol (CAS: 16326-97-9)?
(1R,3S)-1,3-Cyclopentanediol finds applications in various industries. In the ph...
What precautions should be taken when handling N'-[4-(Dimethylamino)phenyl]-N,N-dimethyl-1,4-benzenediamine (CAS: 637-31-0)?
When handling N'-[4-(Dimethylamino)phenyl]-N,N-dimethyl-1,4-benzenediamine, it i...
Are there alternatives to 5-(2,4-Difluorophenyl)-2-methoxypyrimidine (CAS: 1352318-16-1) in synthesis?
There are several alternatives to 5-(2,4-Difluorophenyl)-2-methoxypyrimidine in ...
What regulatory guidelines apply to 1-(3-Methoxyphenoxy)propan-2-ol (CAS: 382141-68-6)?
1-(3-Methoxyphenoxy)propan-2-ol (CAS: 382141-68-6) must comply with the Globally...
Is Tetrodotoxin Citrate (CAS: 18660-81-6) safe?
Tetrodotoxin Citrate is extremely dangerous and should be handled with extreme c...
What are the main uses of 2-Methyl-2-propanyl [(1R,3S)-3-hydroxycyclopentyl]carbamate (CAS: 225641-84-9)?
2-Methyl-2-propanyl [(1R,3S)-3-hydroxycyclopentyl]carbamate (CAS: 225641-84-9) i...
How should waste containing 4-(2-Hydroxyhexafluoroisopropyl)Benzoic Acid (CAS: 16261-80-6) be handled?
Waste containing 4-(2-Hydroxyhexafluoroisopropyl)Benzoic Acid (CAS: 16261-80-6) ...
How is 2-Methyl-2-proanyl {(2S)-1-[(benzyloxy)amino]-3-hydroxy-3-methyl-1-oxo-2-butanyl}carbamate (CAS: 102507-19-7) typically synthesized?
2-Methyl-2-proanyl {(2S)-1-[(benzyloxy)amino]-3-hydroxy-3-methyl-1-oxo-2-butanyl...
What is Benzeneethanamine, α-ethyl-, hydrochloride (1:1) (CAS: 20735-15-3)?
Benzeneethanamine, α-ethyl-, hydrochloride (1:1) is an organic compound with the...
Are there alternatives to 3-{(E)-[4-(Dimethylamino)phenyl]diazenyl}benzoic acid (CAS: 20691-84-3) in synthesis?
In the synthesis of compounds similar to 3-{(E)-[4-(Dimethylamino)phenyl]diazeny...
Source Journal
Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.










![N-[(1S,2R,4S)-2-Amino-4-(dimethylcarbamoyl)cyclohexyl]-N'-(5-chloro-2-pyridinyl)ethanediamide structure N-[(1S,2R,4S)-2-Amino-4-(dimethylcarbamoyl)cyclohexyl]-N'-(5-chloro-2-pyridinyl)ethanediamide structure](https://static.chemtradehub.com/structs/480/480452-37-7-0898.webp)

![N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-beta-phenyl-L-phenylalanine structure N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-beta-phenyl-L-phenylalanine structure](https://static.chemtradehub.com/structs/201/201484-50-6-c2fc.webp)

![N-[(5,6-Dichloro-1H-benzimidazol-2-yl)methyl]-9-(1-methyl-1H-pyrazol-4-yl)-2-(4-morpholinyl)-9H-purin-6-amine structure N-[(5,6-Dichloro-1H-benzimidazol-2-yl)methyl]-9-(1-methyl-1H-pyrazol-4-yl)-2-(4-morpholinyl)-9H-purin-6-amine structure](https://static.chemtradehub.com/structs/238/2387704-62-1-25f4.webp)