Description
(S)-1-Boc-3-methylpiperazine is a hydrophobic compound that is structurally modified from the tetracyclic family of drugs. It has been shown to inhibit tumor cell growth by binding to the oncogene, KRASG12C, and downregulating its expression. This compound also inhibits cancer cell growth through the inhibition of the PI3K/AKT signaling pathway. The pharmacological effects of (S)-1-Boc-3-methylpiperazine are dependent on its ability to bind with high affinity to KRASG12C and inhibit its activity.
Chemical Properties
colorless to yellow liquid
Uses
Reactant involved in the synthesis of biologically activy molecules including:
- CCR5 antagonists with anti-HIV-1 activity
- Opioid receptor antagonists
- Human growth hormone secretagogue receptor antagonists for treatment of obesity
- Fatty acid oxidation inhibitors
Uses
(S)-4-Boc-2-methylpiperazine ((S)-1-Boc-3-methylpiperazine) is a reagent used in the synthesis of benzamide peptidomimetic as non-ATP competitive inihbitors.
Uses
Laboratory chemicals, Manufacture of substances.
Synthesis
At 0 °C, (S)-2-methylpiperazine (400 mg) was dissolved in dichloromethane (20 mL) and di-tert-butyl dicarbonate (871 mg) was slowly added. The reaction mixture was stirred at room temperature for 4 hours. Upon completion of the reaction, the reaction was quenched with deionized water (20 mL) followed by extraction with dichloromethane (2 x 40 mL). The organic phases were combined, washed with saturated sodium chloride solution (40 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to afford (S)-4-N-tert-butoxycarbonyl-2-methylpiperazine as a white solid (669 mg, 84% yield).
References
[1] Organic Process Research and Development, 2018, vol. 22, # 8, p. 978 - 990
[2] Patent: US2008/76758, 2008, A1. Location in patent: Page/Page column 88
[3] Patent: WO2008/70740, 2008, A1. Location in patent: Page/Page column 184
[4] Patent: US2005/261310, 2005, A1. Location in patent: Page/Page column 19
[5] Patent: WO2018/109050, 2018, A1. Location in patent: Paragraph 0226-0230; 0234-0236; 0240-0241
