KR101667480B1 - A pyrazoline-1-carbothioamide naphthochalcone derivative and use of the same for anticancer treatment - Google Patents
A pyrazoline-1-carbothioamide naphthochalcone derivative and use of the same for anticancer treatment Download PDFInfo
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Abstract
The present invention relates to a pyrazoline-1-carbothioamide-based naphtalocalon derivative and its use as an anticancer agent.
Description
The present invention relates to a pyrazoline-1-carbothioamide-based naphtalocalon derivative and its use as an anticancer agent.
Cancer is one of the incurable diseases that humanity needs to solve. In the world, huge capital is invested in development to heal it globally. In Korea, it is the first disease among the causes of death, It is diagnosed and more than 60,000 people are dying. Smoking, ultraviolet rays, chemicals, food, and other environmental factors are among the carcinogens that cause cancer, but the development of therapeutic agents is difficult due to the various causes, and the effects of the therapeutic agents are also different depending on the site where they occur. Currently, substances used as therapeutic agents have considerable toxicity. Since they can not selectively remove only cancer cells, it is urgently necessary to develop a less toxic and effective anticancer drug to prevent the cancer from occurring after cancer development .
Cancer is characterized by "uncontrolled cell growth." These abnormal cell growths form a mass of cells called tumors that penetrate into surrounding tissues and, in extreme cases, to other organs of the body. Academicly, it is also called neoplasia. Cancer is an intractable chronic disease that, even if treated with surgery, radiation, and chemotherapy, in many cases can not be cured, causes pain to the patient, and ultimately leads to death. There are many factors that cause cancer, but they are divided into internal factors and external factors. It is not known exactly how the normal cells transform into cancer cells through the mechanism, but it is known that at least 80 to 90% are affected by external factors such as environmental factors. Internal factors include genetic factors, immunological factors, and external factors include chemicals, radiation, and viruses.
The genes involved in the development of cancer include oncogenes and tumor suppressor genes, which occur when the balance between them is destroyed by the internal or external factors described above. It is classified into blood cancer and solid cancer. It occurs in almost all parts of the body such as lung cancer, stomach cancer, breast cancer, oral cancer, liver cancer, uterine cancer, esophageal cancer and skin cancer. Among the methods used to treat these malignant tumors, chemotherapeutic agents other than surgery or radiation therapy are collectively referred to as anticancer drugs, and most of them exhibit anticancer activity by inhibiting the synthesis of nucleic acids. Chemotherapeutic agents are classified into antimetabolites, alkylating agents, antimitotic drugs, and hormones. Metabolic antagonists that inhibit the metabolic processes required for the proliferation of cancer cells include folic acid (6-mercaptopurine, 6-thioguanine), pyrimidine derivatives (5-fluorouracil, Cytarabine), and DNA is introduced into the DNA guanine to modify the structure of the DNA, Examples of the alkylating agent which exhibits the effect include chlorambucil, cyclophosphamide, ethylene imine compound (thiotepa), alkylsulfonate compound (busulfan), nitrosourea compound (carmustine), triazine compound (dacarbazine ). As a mitotic phase specificity drug, mitotic inhibitors that inhibit mitosis by inhibiting mitosis by inhibiting mitosis include anticancer drugs such as actinomycin D, doxorubicin, bleomycin, mitomycin, vincristine, vinblastine Alkaloids, taxoids, which are mitotic inhibitors including taxane rings, and the like. In addition, hormones such as corticosteroids or progesterone and platinum-containing compounds such as cisplatin are used as anticancer drugs.
The biggest problem with chemotherapy is drug resistance, which is the main factor that ultimately causes treatment failure, despite the initial successful response to chemotherapy. In connection with the problem of overcoming these side effects, efforts are currently being made to find the active ingredient in natural products used in the private sector.
On the other hand, colon cancer is a disease in which cells grow abnormally in the large intestine and penetrate or spread to other tissues. As the diet of our people has become westernized, the incidence rate of cancer has increased in recent years. Surgery through early detection by endoscopy is the best treatment, but the discovery is often delayed, and as with other solid tumors, chemotherapy is needed, and more research is being conducted to develop a more effective treatment.
Polyphenols with plant-derived polyphenols are classified according to the carbon skeleton. Polyphenols having a C6-C3-C6 skeleton are called flavonoids. Most flavonoids are chalcone, Is an open structure in which C3 is composed of an α, β-unsaturated carbonyl group. It is known that chalcone, in which the C3 skeleton is substituted with pyrazolin, has anticancer activity against colon cancer cell lines [Bioorg. Med. Chem. 21: 7018]. Furthermore, it is known that compounds having a carbothioamide group have antibacterial and antidepressant effects [Phosphorus Sulfur Silicon Relat. Elem. 2008, 182, 2409; Arch. Pharm. (Weinheim) 2009, 342, 173].
[Prior Patent Literature]
Korean Patent Publication No. 1020140050952
Disclosure of Invention Technical Problem [8] The present invention has been made in view of the above-mentioned needs, and it is an object of the present invention to provide a novel naphthocalonic acid derivative.
Another object of the present invention is to provide a novel anticancer agent.
In order to accomplish the above object, the present invention provides a compound of the general formula (I) or a pharmaceutically acceptable salt thereof:
[Chemical Formula 1]
Wherein R < 2 > To R 5 And R 2 " to R 5 " are preferably H, or methoxy, but are not limited thereto.
The present invention also provides an anticancer pharmaceutical composition comprising the compound of the present invention and a pharmaceutically acceptable carrier as an active ingredient.
In one embodiment of the present invention, the composition preferably has anticancer effect on colon cancer, but is not limited thereto.
The present invention also provides a food composition for alleviating cancer comprising the compound of the present invention as an active ingredient.
As used herein, "pharmaceutically acceptable salt (s)" includes, but is not limited to, salts of acidic or basic groups that may be present in the compounds used in the compositions. The compounds, which are basic in nature and are included in the present compositions, can form a wide variety of salts with various inorganic and organic acids. Acids that may be used to prepare pharmaceutically acceptable acid addition salts of such basic compounds include those derived from non-toxic acid addition salts such as sulfuric acid, citric acid, maleic acid, acetic acid, oxalic acid, hydrochloride, hydrobromide, hydroiodide, nitrate, , Salicylate, citrate, acid citrate, tartrate, orate, tannate, pantothenate, bitartrate, ascorbate, lactose, citrate, tartrate, phosphate, phosphate, isonicotinate, acetate, lactate, salicylate, citrate, , Succinate, maleate, gentisinate, fumarate, gluconate, glucaronate, saccharate, formate, benzoate, glutamate, methanesulfonate, ethanesulfonate, benzenesulfonate, p- toluenesulfonate and Pamoate (i.e., 1,1'-methylene-bis- (2-hydroxy-3-naphthoate)) salt But it is those which form a salt containing a pharmaceutically acceptable anion that is not limited to these ever. Compounds included in the present compositions comprising amino moieties may form pharmaceutically or cosmetically acceptable salts with various amino acids in addition to the acids described above. The compounds contained in the composition, which are acidic in nature, can form base salts with various cations which are pharmaceutically or cosmetically acceptable. Examples of such salts include alkali metal or alkaline earth metal salts, especially calcium, magnesium, sodium, lithium, zinc, potassium and iron salts.
In certain embodiments, the term "pharmaceutically acceptable" means that it is listed for use in animals, particularly humans, in a pharmacopeia or other generally known pharmacopoeia. The term "carrier " refers to a diluent, adjuvant, excipient, or vehicle to be administered with a compound of the present invention. Such pharmaceutical carriers may be liquids such as water and oils, including petroleum, animal, vegetable or synthetic oils such as peanut oil, soybean oil, mineral oil, sesame oil and the like. The pharmaceutical carrier may be saline, gum arabic, gelatin, starch paste, talc, keratin, colloidal silica, urea, and the like. Adjuvants, stabilizers, thickeners, lubricants and coloring agents may also be used. When administered to a patient, the pillrol compound and the pharmaceutically acceptable carrier are preferably sterile. When the compound of the present invention is administered intravenously, water is a preferred carrier. Particularly in the case of injection solutions, brine solutions and aqueous dextrose and glycerol solutions can be used as liquid carriers. Suitable pharmaceutical carriers also include starch, glucose, lactose, sucrose, gelatin, malt, rice, flour, chalk, silica gel, sodium stearate, glycerol monostearate, talc, sodium chloride, dried skimmed milk, glycerol, , Water, ethanol, and the like. The composition may also contain minor amounts of wetting or emulsifying agents, or pH buffering agents, if desired.
The cancer includes common cancer diseases and is preferably used for the treatment of gastric cancer, colon cancer, breast cancer, lung cancer, non-small cell lung cancer, bone cancer, pancreatic cancer, skin cancer, head or neck cancer, skin or intraocular melanoma, uterine cancer, Hodgkin's disease, esophageal cancer, small intestine cancer, endocrine cancer, thyroid cancer, pituitary cancer, adenocarcinoma, soft tissue sarcoma, urethral cancer, uterine cancer, uterine cancer, endometrial cancer, uterine cancer (CNS) tumors, primary CNS lymphoma, spinal cord tumors, brain tumors, lymph nodes, lymph nodes, kidney or ureteral cancers, renal cell carcinomas, renal pelvic carcinomas, Glioma, pituitary adenoma, and the like, and particularly includes all cancers caused by cancer cells having multidrug resistance to existing anticancer drugs.
The compositions of the present invention may be formulated into a variety of carriers and delivery systems. The amount of therapeutic compound administered and the concentration of the compound will depend on the vehicle or device selected, the clinical condition of the patient, side effects and the formulation stability of the compound. Thus, the physician will use the appropriate formulation containing the appropriate concentration of the therapeutic compound, and will select the dosage form according to clinical experience with the patient or similar patient in question.
In addition, excipients may be used in the formulation. Examples include co-solvents, surfactants, oils, wetting agents, emollients, preservatives, stabilizers and antioxidants. As a pharmaceutically acceptable buffer, for example, a tri or phosphate buffer may be used. Effective amounts of diluents, additives and excipients are amounts effective to obtain pharmaceutically acceptable formulations in terms of solubility, bioactivity, and the like.
Thus, the compositions of the present invention include conventional, pharmaceutically acceptable vehicles for topical, oral or parenteral administration, and therapeutic compounds that can be formulated. The formulations may also contain minor amounts of adjuvants, such as buffers and preservatives, to maintain isotonicity, physiological and pH stability.
The compositions of the present invention may be administered to both human and animal subjects.
The compositions of the present invention may be administered in a composition wherein the active compound is intimately mixed with one or more inactive ingredients and optionally one or more additional active ingredients. The compositions can be used as any composition for human and animal administration known in the art.
The composition of the present invention may be administered according to a proper route depending on the dosage form. For example, the subject can be administered intravenously, intraarterially, subcutaneously, intramuscularly, and the like.
For oral administration, either solid or fluid unit dosage forms may be prepared. The aqueous form may be dissolved in an aqueous vehicle together with a sugar, an aromatic flavor and a preservative to produce a syrup. Elsys are prepared using suitable sweeteners such as aromatic flavors, sugars and saccharin, and hydro-alcoholic (e.g., ethanol) vehicles. Suspensions can be prepared using aqueous vehicles, such as acacia, tragacanth, methylcellulose, and the like. The synthetic compound of the present invention may be formulated with a stabilizing agent, for example, a metal chelator reducing agent such as ethylenediaminetetraacetic acid (EDTA), or a reducing agent such as sodium metabisulfite.
Suitable formulations for parenteral administration will be apparent to those skilled in the art. Generally, the therapeutic compound is prepared in aqueous solution at a concentration of about 1 to about 100 mg / mL. More typically, the concentration is about 10 to 60 mg / mL or about 20 mg / mL. Depending on the stability and efficacy of the compound selected for use, in some cases concentrations below 1 mg / mL may be necessary.
The effective dose of the active ingredient of the present invention will depend, at least, on the nature of the therapeutic condition, the toxicity, whether the compound is used prophylactically (with less dosage) or against an active cancer infection, the delivery method and the pharmaceutical formulation , Will be determined by the clinician using conventional dose escalation studies. The dose is generally from about 0.0001 to about 100 mg / kg body weight per day, generally from about 0.01 to about 10 mg / kg body weight per day, more usually from about 0.01 to about 5 mg / kg body weight per day, more usually from 1 Day to about 0.05 mg / kg body weight per day. For example, a daily dosage for an adult weighing about 70 kg will be from 1 mg to 1000 mg, preferably from 5 mg to 500 mg, and may be single or multiple dosage forms.
The sterile formulations are suitable for a variety of parenteral routes including intraperitoneal, intraarticular, intramuscular, intravascular, intravenous, inhalation and subcutaneous.
A slow or extended release delivery system comprising any of a number of biopolymers (bio-based systems), liposome systems and polymer delivery systems, such as dendrimers, can be utilized in the compositions herein to provide a continuous or long term source Can be provided. Such slow release systems are applicable for topical, ocular, oral and parenteral formulations.
The synthetic compound (s) of the present invention may also be formulated as a nutraceutical or a nutraceutical. For example, the synthetic compound (s) can be formulated into oral use foods such as cereal, fruit juices, alcoholic beverages, bread, and the like.
Hereinafter, the present invention will be described.
The present invention was designed to synthesize naphthocalkon derivatives having a pyrazoline group and a carbothioamide group to synthesize a total of 18 derivatives and to inhibit the growth of colon cancer cells at a concentration of several hundred nanomolar (nM).
As can be seen from the present invention, the derivatives of the present invention can inhibit the growth of colorectal cancer cells at a concentration level of several hundred nanomolar (nM) and can be used as anticancer candidate substances.
1 is a schematic diagram of a method for synthesizing a pyrazoline-1-carbothioamide-based naphtalocalon derivative
Figure 2 shows the basic structure of a pyrazoline-1-carbothioamide-based naphtalocalon derivative
FIGS. 3A to 3C are graphs showing the inhibition of the proliferation of HCT116 colon cancer cells by the pyrazoline-1-carbothioamide-based naptocalkon derivative. The cells were treated with colon cancer cell lines at concentrations of 0, 50, 500 and 5,000 nM As a result,
4 to 57 are graphs showing the results of 1H-NMR, 13C-NMR, Mass Spectrum data
The present invention will now be described in more detail by way of non-limiting examples. The following examples are intended to illustrate the present invention and the scope of the present invention is not to be construed as being limited by the following examples.
Example 1 : Pyrazoline -One- Carbothioamide system Naphthocalcone Method for synthesizing derivatives
In the present invention, were synthesized benzochalcone (III) through a 1-Hydroxy- 2-acetonaphone (I ) and methoxy substituted Claisen-Schmidt reaction between a benzaldehyde (II) derivative as illustrated in Figure 1, these re-hydrazine (NH 2 NH 2 ) to pyrazoline (IV), and pyrazole-carbothioamides were synthesized by reaction with corresponding methoxybenzoisothiocyanate (V).
A detailed experimental procedure is shown by way of example for the derivative 305. 1-Hydroxy-2-acetonaphone (1.86 g, 10 mmol) and 2-methoxybenzaldehyde (1.36 g, 10 mmol) were dissolved in 50 ml of ethanol solvent and the temperature of the reaction mixture was lowered to 3-4 ° C using an ice structure. 10 ml of 50% (w / v) KOH aqueous solution is slowly added to the above cooled reaction mixture, the ice structure is removed, the temperature of the reaction mixture is raised to room temperature, and the mixture is stirred at the same temperature for about 24 hours. ? After confirming that the reaction is terminated by chromatography, the reaction mixture is added to 300 ml of ice water and then acidified with 6N hydrochloric acid (pH = 3). The solid formed in the course of acidification is obtained by filtration under reduced pressure, and this solid is recrystallized in a methanol solvent to obtain pure chalcone (60%, 156-158 ° C). After dissolving the obtained chalcone (1.5 g, 5 mmol) in 30 ml of ethanol, excess hydrazine monohydrate (1 ml of 64-65% solution, 13 mmol) was added and refluxed at 90 ° C for about 6 hours. The reaction mixture was cooled to room temperature and the solid pyrazoline formed was obtained by filtration under reduced pressure and used in the next reaction. 2,4-di-methoxyisothiocyanate (100 mg, 0.5 mmol) and pyrazoline (160 mg, 0.5 mmol) were dissolved in ethanol (15 ml) and refluxed at 90 ° C for about 2 hours. After the reaction mixture was cooled to room temperature, the solid formed was filtered under reduced pressure to obtain the target compound pyrazoline-carbothioamide ( 305 ; 74%, 223-224 ° C).
In the case of the method for synthesizing the remaining derivatives of the present invention, the basic structure of the derivative is the same as that of the derivative 305, and since there is only a difference between the corresponding starting material and the intermediate, it is not described in detail. .
Example 2 : Pyrazoline -One- Carbothioamide system Naphthocalcone Derivative Nuclear magnetic resonance spectroscopy Experiment
To confirm the synthesized pyrazoline-1-carbothioamide-based naphtalocalon derivative, nuclear magnetic resonance spectroscopy was applied. The instrument used was a Bruker Avance 400 (Bruker, Karlsruhe, Germany) , The compound was dissolved in a solvent of dimethylsulfoxide-d6 (DMSO-d6), transferred to a 2.5-mm NMR tube, and measured at room temperature. The hydrogen nuclear magnetic resonance spectroscopy (1 H-NMR) was performed at 400 MHz, and the carbon nuclear magnetic resonance spectroscopy (13 C-NMR) was conducted at 100 MHz. Detailed experimental methods were used [Magn. Reson. Chem. 51: 593]. Pyrazoline-1-carbothioamide-based naphthocalkon derivatives, and the names of the 18 types of pyrazoline-1-carbothioamide-based naphthocalcholine derivatives are shown in the following table same. Mass spectrometry (MS) was performed to confirm the structure confirmation, and JMS700 spectrometer (JEOL, Tokyo, Japan) was used.
(calcd./found)
Here, the * marks shown in the results of mass spectrometry are the results measured at negative molecular ions, and the results without * marks are the results measured at positive molecular ions.
Hydrogen Nuclear Magnetic Resonance Spectroscopy and Carbon Nuclear Magnetic Resonance Spectroscopy of pyrazoline-1-carbothioamide-based naphthocalkon derivatives are shown in the table below.
4.16 (dd, 18.0, 11.7)
4.13 (dd, 18.0, 11.7)
4.02 (dd, 17.7, 11.4)
4.14 (dd, 18.0, 11.7)
4.13 (dd, 17.9, 11.9)
4.15 (dd, 18.0, 11.8)
4.06 (dd, 17.8, 11.3)
3.94 (dd, 17.7, 11.4)
4.05 (dd, 17.9, 11.3)
4.05 (dd, 17.8, 11.3)
4.04 (dd, 17.8, 11.2)
4.05 (dd, 17.8, 11.3)
4.12 (dd, 18.0, 11.4)
4.12 (dd, 18.0, 11.4)
4.11 (dd, 18.1, 11.4)
4.10 (dd, 18.0, 11.4)
4.10 (dd, 18.0, 11.4)
4.11 (dd, 18.0, 11.4)
Example 3 : Pyrazoline -One- Carbothioamide system Naphthocalcone Inhibitory effect of derivatives on colon cancer cell lines
HCT116 human colorectal cancer cells were purchased from the American Type Culture Collection (ATTC) and DMEM (Invitrogen Life Technologies) culture medium containing 10% FBS (Fetal Bovine Serum, Invitrogen Life Technologies) and Antibiotic-Antimycotic solution Were cultivated in a 5% CO2 incubator at 37 ° C in a 100-mm cell culture dish at a seeding density of 1 × 10 6 . The effect of inhibiting cell proliferation was determined by analyzing the effect of colonogenic assay of cancer cells by pyrazoline-1-carbothioamide-based naphtalocalon derivative. HCT116 cells were treated with 6,000 cells per well in a 24-well culture dish, treated with pyrazoline-1-carbothioamide-based naphtalocalone derivative, and after 7 days, 6% glutaraldehyde and 0.5% The mixture was mixed with a crystal violet solution (1: 1) and added to the cells. The cells were allowed to react for 15 minutes to stain the remaining cells. The growth inhibitory ability of HCT116 colon cancer cells by the
The concentration (GI50) which inhibited the growth of colon cancer cell line was obtained at 50% level of each derivative.
Namely, pyrazoline-1-carbothioamide-based naphtalocalon derivatives showed 50% inhibition of growth of colon cancer cell lines at a concentration of at least 5 uM.
1H-NMR, 13C-NMR and Mass Spectrum of the pyrazoline-1-carbothioamide-based naphthocalkon derivatives are shown in FIG. 4 to FIG.
Claims (5)
[Chemical Formula 1]
In Formula 1,
R 2 and R 4 are methoxy, R 3 , R 5 and R 2 " to R 5" are H;
R 2 , R 4 and R 3 " are methoxy and R 3 , R 5 , R 2" , R 4 " and R 5" are H;
R 2 , R 4 and R 3 " to R 5" are methoxy and R 3 , R 5 and R 2 " are H;
R 3 and R 5 are methoxy, R 2 , R 4 and R 2 " to R 5" are H;
R 3 , R 5 and R 3 " are methoxy, and R 2 , R 4 , R 2" , R 4 " and R 5" are H;
R 3 , R 5 and R 4 " are methoxy and R 2 , R 4 , R 2" , R 3 " and R 5" are H; And
R 3 , R 5 and R 3 " to R 5" are methoxy and R 2 , R 4 and R 2 " are H.
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