Bismuth (Ⅲ) complexes of substituted piperidine dicarbamates and their preparation methods and their application in the preparation of antitumor drugs
A technology of bismuth piperidinamide and anti-tumor drugs, applied in the field of anti-tumor drugs, can solve the problems of few anti-tumor cell lines, single structure, low clinical application value, etc., achieves significant tumor inhibitory activity, wide application prospects, The effect of good antitumor activity
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Embodiment 1
[0025] Example 1: 2-methylpiperidine bismuth dicarbamate and its preparation
[0026] Add 0.496g (5mmol) 2-methylpiperidine, 1.01g (10mmol) triethylamine, 15mL anhydrous methanol into a round bottom flask, stir and dissolve with magnetic force, put in a cold water bath at 0-5℃, add 0.76g dropwise (10mmol)CS 2 , magnetically stirred for 5 h.
[0027] 0.53g (1.7mmol) BiCl 3 Dissolve in 15 mL of anhydrous methanol, drop into the above reaction solution, stir at room temperature for 3 h, filter with suction, wash with anhydrous methanol, and dry in vacuo. The solid was recrystallized from acetonitrile to obtain 0.75 g of yellow crystals, yield 61.5%, melting point: 194-195°C, number N056.
[0028] 1 HNMR (400 MHz, CDCl 3 ), δ: 1.303~1.320 (9H, d, -CH 3 , J=6.8Hz), 1.627~1.715 (6H, m, Py-CH 2 , J=3.6-7.2Hz), 1.742~1.822 (6H, m, Py-CH 2 , J=4.4-7.6Hz), 2.163~2.213 (6H, m, Py-CH 2 , J=4.0-6.8Hz), 3.105~3.177(6H, q, N-CH 2 , J=7.2Hz),4.978~5.122 (3H, m, N-CH , J=6.0-9.6Hz)...
Embodiment 2
[0030] Example 2: 3-ethoxycarbonylpiperidine bismuth dicarbamate and its preparation
[0031] Add 0.786 g (5 mmol) of ethyl 3-piperidinecarboxylate, 0.25 g (6 mmol) of sodium hydroxide, and 15 mL of anhydrous methanol into a round-bottomed flask. After magnetic stirring and dissolution, add 0.76 g ( 10mmol) CS 2 , magnetically stirred for 5 h.
[0032] 0.53 g (1.7 mmol) BiCl 3 Dissolve in 15 mL of anhydrous methanol, drop into the above reaction solution, stir at room temperature for 3 h, filter with suction, wash with anhydrous methanol, and dry in vacuo. The solid was purified on a column, eluent: ethyl acetate-petroleum ether = 1:2, and 1.09 g of yellow powder solid was isolated, yield 72.2%, melting point: 83-85°C.
[0033] 1 HNMR (400 MHz, CDCl 3 ), δ: 1.245~1.281 (9H, t, -CH 3 , J=7.2Hz), 1.662~1.754 (6H, m, Py-CH2 , J=9.2Hz), 1.835~1.911 (3H, m, Py-CH, J=7.6Hz), 2.251~2.327 (3H, m, Py-CH, J=7.6Hz), 2.643~2.696 (3H, m , Py-CH,J=7.2Hz), 3.040~3.232 (6H, t t, N-CH ...
Embodiment 3
[0035] Example 3: 4-(1-Pyrrolidinyl) Bismuth Dicarbamate and Its Preparation
[0036] Add 0.771 g (5 mmol) 4-(1-pyrrolidinyl) piperidine, 0.25 g (6 mmol) sodium hydroxide, and 15 mL of anhydrous methanol into a round bottom flask, stir and dissolve with magnetic force, and place in a cold water bath at 0-5°C , add dropwise 0.76 g (10 mmol) CS 2 , magnetically stirred for 2 h, and then stirred for 4 h at room temperature.
[0037] 0.53 g (1.7 mmol) BiCl 3 Dissolve in 15 mL of anhydrous methanol, drop into the above reaction solution, stir at room temperature for 3 h, filter with suction, wash with anhydrous methanol, and dry in vacuo. The solid was purified on a column, eluent: ethyl acetate-petroleum ether=1:3, and 0.86 g of yellow powder solid was isolated, with a yield of 57.5%. Melting point: 138-140°C, number N057.
[0038] 1 HNMR (400 MHz, CDCl 3 ), δ: 1.625~1.720 (6H, m, Py-CH 2 , J=3.6-10.8Hz),1.777~1.891 (12H, t, Cy-CH 2 , J=4.0-8.4Hz), 1.964~2.005 (6H, d d, Py...
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