Synthesis of optically active nicotinoids

Chavdarian, Charles G.; Sanders, Edward B.; Bassfield, Ronald L.

doi:10.1021/jo00345a034

Cited by 31 publications

(7 citation statements)

References 5 publications

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“…Chavdarian and co‐workers reported the first synthesis of ( S )‐nicotine (Scheme 28). [103] Amino alcohol 106 , which was converted by L‐proline as the starting material, was treated with SOCl 2 and NaHCO 3 /NaCN to give 108 . Hydroxy compound 110 was afforded by the treatment of 108 with lithium diisopropylamide (LDA), followed by the addition of the 3‐ethoxyacrolein ( 109 ) to the resultant anion, which was then treated with HBr/HOAc to give 2‐bromonicotine ( 111 ).…”

Section: Synthetic Strategy Of Nicotinementioning

confidence: 99%

Research Progress in the Pharmacological Effects and Synthesis of Nicotine

Zhang

Song

et al. 2022

ChemistrySelect

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Nicotine is an alkaloid found in solanaceae plants and an important component in tobacco. It is the main substance that causes smoking addiction and can have many effects on the nervous system. In recent years, nicotine has been found to have the value of drug transformation research, which has attracted the attention of a large number of scholars in the fields of organic synthesis and medicinal chemistry. Related drug transformation research and chemical synthesis continue to emerge. This article mainly summarizes the research progress of nicotine pharmacological effects and synthesis.

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Section: Synthetic Strategy Of Nicotinementioning

confidence: 99%

Research Progress in the Pharmacological Effects and Synthesis of Nicotine

Zhang

Song

et al. 2022

ChemistrySelect

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“…25 °C for 1 h furnished 14 in 91% yield. The formation of 3-chloropiperidine derivative 14 may be visualized by the reaction of SOCl 2 with prolinol derivative 13 to furnish 3-chloromethylpyrrolidine derivative 13a which can undergo intramolecular displacement reaction by the attack of nitrogen to give an aziridine intermediate 14a (Scheme ) . The chloride ion can attack intramolecularly to furnish a strain-free 3-chloropiperidine derivative 14 .…”

Section: Chemistrymentioning

confidence: 99%

Novel Antidiabetic and Hypolipidemic Agents. 3. Benzofuran-Containing Thiazolidinediones

Reddy

Bhushan

et al. 1999

J. Med. Chem.

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Several thiazolidinedione derivatives having 5-hydroxy-2,3-dihydro-2, 2,4,6,7-pentamethylbenzofuran moieties and their 5-benzyloxy derivatives and 5-hydroxy-2,4,6,7-tetramethylbenzofuran moieties were synthesized and evaluated in db/db mice. Insertion of an N-Me group into the linker between thiazolidinedione and substituted benzofuran pharmacophores showed considerable improvement in their euglycemic activity. Further improvement has been observed when a pyrrolidine moiety is introduced in the structure to give 5-[4-[N-[3(R/S)-5-benzyloxy-2,3-dihydro-2,2,4,6, 7-pentamethylbenzofuran-3-ylmethyl]-(2S)-pyrrolidin-2- ylmethoxy]pheny lene]thiazolidine-2,4-dione (21a). At a 100 mg/kg/day dose of the maleate salt, compound 21a reduced the plasma glucose and triglyceride to the level of lean littermate, i.e. 8 +/- 1 mM, and is the most potent and efficacious compound reported in this series.

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“…[14][15][16][17] Conversely, the construction of the pyridine ring from a 2-substituted pyrrolidine (S-proline) has been reported. 18 In recent years, the structural modification of nicotine has been thoroughly investigated by Comins. [19][20][21][22] The Comins approach to prepare substituted nicotine derivatives was elegantly employed in the shortest enantioselective synthesis of Altinicline (5-ethynyl-nicotine), 23 a drug employed for the treatment of Parkinson's disease.…”

Section: Introductionmentioning

confidence: 99%