Application of thiourea molecule in preparation of antitumor drugs

A technology of antineoplastic drugs and thioureas, which is applied in the direction of antineoplastic drugs, drug combinations, medical preparations containing active ingredients, etc., can solve the problems of toxic and side effects, achieve less toxic and side effects, convenient operation, and good thermal stability Effect

Active Publication Date: 2016-05-18
杭州墨丘利生物医药科技有限公司
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, while they can effectively kill tumor cells, they also have toxic side effects on normal tissues, thus limiting the application of these thiourea derivatives

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Application of thiourea molecule in preparation of antitumor drugs
  • Application of thiourea molecule in preparation of antitumor drugs
  • Application of thiourea molecule in preparation of antitumor drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1 n-butylthiourea

[0035]

[0036] Add n-butylamine (0.735 mL, 7.4 mmol) into 10 mL of dichloromethane, slowly add benzoyl isothiocyanate (0.9 mL, 6.7 mmol) dropwise, and stir overnight at room temperature. After concentration, 10 mL of methanol was added, followed by 3 mL of 5M NaOH in methanol. After stirring for 3 hours, concentrate and pass through the column to obtain colorless crystals of n-butylthiourea with a yield of 81%. 1 H-NMR (400MHz, CDCl 3 ) (mixture of isomers): δ=0.94(t,3H), 1.36-1.44(m,2H), 1.56-1.64(m,2H), 3.20(brs,2H), 6.01(brs,2H), 6.58 (brs,1H).ESI-TOF-MSm / z:[M-H] - , The theoretical value is 131.22, and the actual value is 131.3.

Embodiment 2

[0037] Embodiment 2N, N'-(1,2-ethylene) dithiourea

[0038]

[0039] Ethylenediamine (0.27g, 4.5mmol) was added into 10mL of dichloromethane, benzoyl isothiocyanate (1.42mL, 10.6mmol) was slowly added dropwise, and stirred overnight at room temperature. After filtering and washing with n-hexane, a light yellow solid was obtained. To this pale yellow solid (1.04 g, 2.68 mmol), 10 mL of methanol was added, and then 3 mL of 5M methanolic NaOH solution was added. After stirring for 3 hours, it was filtered and washed with ice methanol to obtain white solid 1,2-ethyldithiourea with a yield of 85%. 1 H-NMR (400MHz, DMSO-d6) (mixture of isomers): δ=3.12(s,1.46H),3.47(s,2.54H),7.02-7.69(br,6H).ESI-TOF-MSm / z:[M+H] + , The theoretical value is 179.03, and the actual value is 178.9.

Embodiment 3

[0040] Embodiment 3N, N '-[1,3-(2-hydroxypropyl)] dithiourea

[0041]

[0042] 1,3-Diamino-2-propanol (0.37g, 4.1mmol) was added to 10mL of dichloromethane, slowly added dropwise to benzoyl isothiocyanate (1.58g, 9.7mmol), stirred at room temperature After 2 hours, filtration gave a pale yellow solid. The light yellow solid was added to 10 mL of methanol, and then 3 mL of 5M methanolic NaOH solution was added, and stirred overnight at room temperature. After concentration, the pure product 1,3-(2-hydroxypropyl)dithiourea was obtained by passing through the column with a yield of 70%. 1 H-NMR (400MHz,D 2 O) (mixture of isomers): δ=3.19(s,1H), 3.28(s,1H), 3.48(s,1H), 3.61(s,1H), 3.99(m,1H). 1 H-NMR (400MHz, DMSO-d6) (mixture of isomers): δ=2.99-3.99(br,1H),3.46(brs,2H),3.72(s,1H),5.15(br,1H),7.06 (brs,4H),7.44-7.55(br,2H).ESI-TOF-MSm / z:[M+H] + , The theoretical value is 209.04, and the actual value is 209.1.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention discloses application of a thiourea molecule in preparation of antitumor drugs. The structural formula of the thiourea molecule is selected from formula I to formula IV, wherein R1, R2 and R3 are independently selected from hydrogen, alkyl with a carbon number of 1-10, aryl or a heteroatom group containing N, O and S. The invention provides new application of the thiourea molecule, specifically in preparation of anticancer drugs. The thiourea molecule is adopted as the anti-cancer drug, or is used as the active ingredient for preparation of pharmaceutical preparations, the antitumor drugs show very low cytotoxicity to human lung adenocarcinoma cells (A549), human breast cancer cells (BCap-37), human oral epidermoid carcinoma cells (KB), human lung fibroblast (HFL1) and human bronchial epithelial cells (BEAS-2B), but has very good antitumor effect at the animal level. (formula I, formula II, formula III, and formula IV).

Description

technical field [0001] The invention relates to the field of anticancer drugs, in particular to the application of a thiourea molecule in the preparation of antitumor drugs. Background technique [0002] Thiourea compounds (TUs) refer to a class of compounds with thiourea groups (-NH-CS-NH-, TU) in their molecular structures. Such compounds generally have broad-spectrum antibacterial, bactericidal, and antiviral properties (Liu, J, Yang, S, Li, X, et al., Synthesis and antiviral bioactivity of chiralthioureas containing leucine and phosphonate moieties. Molecules 2010, 15:5112-5123.). Some of these compounds have anti-HIV activity (Venkatachalam, T, Mao, Cand Uckun, FM, Effect of stereochemistry on the anti-HIV activity of chiralthiourea compounds. Bioorganic & Medicinal Chemistry 2004, 12:4275-4284.). Disclose a kind of water-soluble anionic polythiourea molecule in the Chinese patent document that publication number is CN1138323A, this polythiourea molecule has anti-human...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/17A61K31/198A61P35/00
Inventor 陈忠春
Owner 杭州墨丘利生物医药科技有限公司
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap