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Gossypol derivatives and preparation thereof, application of gossypol derivatives in pesticide and anti-cancer activity

A kind of derivative, gossypol technology, applied in gossypol derivatives and their preparation, in the field of pesticide application and anticancer activity, to achieve non-target biosafety, good environmental compatibility, and significant anti-plant virus activity.

Active Publication Date: 2016-08-24
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But so far, no chemical pesticide can completely cure a plant once it is infected with TMV

Method used

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  • Gossypol derivatives and preparation thereof, application of gossypol derivatives in pesticide and anti-cancer activity
  • Gossypol derivatives and preparation thereof, application of gossypol derivatives in pesticide and anti-cancer activity
  • Gossypol derivatives and preparation thereof, application of gossypol derivatives in pesticide and anti-cancer activity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Example 1: Gossypol-methylamine Schiff base (I a -1) Synthesis

[0043]

[0044] In a 100 mL round-bottom flask, add 0.50 g (0.86 mmol) of gossypol acetate and 40 mL of absolute ethanol, and then add 0.05 g (1.73 mmol) of methylamine after the solution is completely dissolved. The reaction solution was heated to reflux for 5 hours. After being naturally cooled to room temperature, the reaction solution was filtered to obtain a bright yellow solid. Yield, 96%; melting point: 258-259°C; 1 H NMR(400MHz, DMSO-d 6 )δ13.04(dd, J=13.0, 4.6Hz, 2H), 9.73(d, J=13.0Hz, 2H), 8.39(s, 2H), 7.84(s, 2H), 7.45(s, 2H), 3.75-3.66(m, 2H), 3.27(d, J=4.6Hz, 6H), 1.93(s, 6H), 1.43(t, J=6.4Hz, 12H); 13 C NMR(100MHz, DMSO-d 6 )δ171.47,163.60,149.58,146.22,131.07,126.74,126.13,119.96,116.44,115.81,103.08,36.84,26.46,20.34,20.31,20.17; HRMS(ESI)m / z calcd for C 32 H 37 N 2 O 6 [M+H] + 545.2646, found 545.2645.

Embodiment 2

[0045] Example 2: Gossypol fatty amine Schiff base derivative I a -2-I a -16, I a -23, gossypol oxime, hydrazone Schiff base derivative I b -3-I b Synthesis of -7: Completed by repeating the method of Example 1

[0046] Compound I a -2: The specific operation is carried out according to operation step A. Yellow solid; yield, 96.1%; melting point 240-241°C; 1 H NMR(400MHz, CDCl 3 )δ13.38-13.35(m, 2H), 9.64(d, J=12.7Hz, 2H), 8.01(s, 2H), 7.60(s, 2H), 5.57(s, 2H), 3.71-3.75(m , 2H), 3.52-3.43 (m, 4H), 2.12 (s, 6H), 1.69-1.78 (m, 4H), 1.50-1.55 (m, 12H), 1.00 (t, J = 7.2 Hz, 6H); 13 C NMR(100MHz, CDCl 3 )δ172.44,163.03,148.91,147.19,131.70,128.89,127.15,118.16,115.63,114.72,103.02,52.50,27.42,23.91,20.40,20.34,20.07,11.14; HRMS(ESI)m / z calcd for C 36 H 45 N 2 O 6 [M+H] + 601.3272, found 601.3271.

[0047] Compound I a -3: The specific operation is carried out according to operation step A. Bright yellow solid; Yield, 89.6%; Melting point: 234-235°C; 1 H NMR(400MHz, CDCl 3 )δ13.41-13....

Embodiment 3

[0067] Example 3: Gossypol-2-sulfonate sodium ethylamine Schiff base (I a -18) Synthesis:

[0068]

[0069] In a 100mL round-bottomed flask, add 0.069g (1.73mmol) of sodium hydroxide, 40mL of absolute ethanol, and 0.22g (1.73mmol) of taurine. Heat at reflux for 1h to generate sodium salt (pH value is about 8), then add 0.50 g (0.86 mmol) of gossypol acetate, heating for 5 hours, cooling to room temperature, suction filtration, recrystallization with isopropanol and methanol to obtain the target compound. Yield, 94.0%; melting point>300℃; 1 H NMR(400MHz, DMSO-d 6 )δ13.07-12.95(m, 2H), 10.03(d, J=11.2Hz, 2H), 8.51(s, 2H), 7.28(s, 2H), 3.78(d, J=3.8Hz, 4H), 3.72-3.62 (m, 2H), 2.82 (t, J=5.5Hz, 4H), 1.95 (s, 6H), 1.46-1.41 (m, 12H). 1 H NMR (400MHz, CD 3 OD)δ9.90(s, 2H), 7.56(s, 2H), 3.99(t, J=6.3Hz, 4H), 3.82-3.74(m, 2H), 3.18(t, J=6.3Hz, 4H) , 2.05 (s, 6H), 1.54-1.50 (m, 12H). 13 C NMR(100MHz, DMSO-d 6 )δ171.33, 161.82, 152.46, 146.34, 131.01, 126.79, 126.29, 121.87, 116.34, 114.7...

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Abstract

The invention relates to gossypol derivatives and preparation method thereof and application of the gossypol derivatives in plant virus prevention and control, insecticidal action, bactericidal action and anti-cancer action, wherein the significance of all groups in a formula is shown in the description. The gossypol derivatives show the excellent anti-plant virus activity, bactericidal activity, insecticidal activity and anti-cancer activity.

Description

technical field [0001] The present invention relates to gossypol derivatives and their preparation, application in pesticides and anticancer activity. Background technique [0002] Gossypol (structural formula 1) mainly exists in cottonseed, accounting for 0.4%-1.7% of the total weight of cottonseed. Gossypol has a very wide range of biological activities: almost all cancer cells have inhibitory activity; can inhibit a variety of viruses, such as HIV, avian influenza, etc., which are now difficult to treat; have anti-parasitic activity (malaria, trypanosomiasis, etc.) ; It has bactericidal and insecticidal activity, and the content of gossypol compounds in the cotton plant and the ratio of different substances will be affected by external bacteria and insects; it also has antioxidant activity, and it has also shown its application in rubber and chemical fields etc. (Xu Zhihong, China Oils, 2008, 33(8), 6-10). Gossypol is considered to be a part of the defense system of cot...

Claims

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Application Information

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IPC IPC(8): C07C225/24C07C225/16C07D213/38C07D307/14C07C323/25C07C255/61C07C255/24C07C309/14C07C311/32C07C317/28C07F9/40C07C251/48C07C251/86C07C311/49C07C50/38C07C251/24C07D277/42C07C69/21C07C43/23C07C255/55C07D261/20A61P35/02A61P35/00A01P7/04A01P3/00A01P1/00A01P13/00
Inventor 汪清民李玲刘玉秀王兹稳李永强
Owner NANKAI UNIV
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