CN109803656A - 一种抗白色念珠菌的新型化合物及其制备方法和应用 - Google Patents
一种抗白色念珠菌的新型化合物及其制备方法和应用 Download PDFInfo
- Publication number
- CN109803656A CN109803656A CN201780025353.9A CN201780025353A CN109803656A CN 109803656 A CN109803656 A CN 109803656A CN 201780025353 A CN201780025353 A CN 201780025353A CN 109803656 A CN109803656 A CN 109803656A
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- Prior art keywords
- candida albicans
- compound
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- reaction
- piperazine
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- 229940095731 candida albicans Drugs 0.000 title claims abstract description 57
- 230000001032 anti-candidal effect Effects 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 241000222122 Candida albicans Species 0.000 claims abstract description 34
- 239000003814 drug Substances 0.000 claims abstract description 14
- 229940079593 drug Drugs 0.000 claims abstract description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 31
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 26
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 14
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 13
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 8
- 208000035473 Communicable disease Diseases 0.000 claims description 7
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- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 150000004885 piperazines Chemical class 0.000 claims description 6
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- 238000001816 cooling Methods 0.000 claims description 3
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- 239000012074 organic phase Substances 0.000 claims description 3
- MRDGZSKYFPGAKP-UHFFFAOYSA-N para-methoxyphenylpiperazine Chemical compound C1=CC(OC)=CC=C1N1CCNCC1 MRDGZSKYFPGAKP-UHFFFAOYSA-N 0.000 claims description 3
- 238000004064 recycling Methods 0.000 claims description 3
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 229940125904 compound 1 Drugs 0.000 description 10
- 229940125782 compound 2 Drugs 0.000 description 9
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 231100000135 cytotoxicity Toxicity 0.000 description 6
- 230000003013 cytotoxicity Effects 0.000 description 6
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- PAWGRNGPMLVJQH-KHPPLWFESA-N cis-2-dodecenoic acid Chemical compound CCCCCCCCC\C=C/C(O)=O PAWGRNGPMLVJQH-KHPPLWFESA-N 0.000 description 5
- RFHAOTPXVQNOHP-UHFFFAOYSA-N fluconazole Chemical compound C1=NC=NN1CC(C=1C(=CC(F)=CC=1)F)(O)CN1C=NC=N1 RFHAOTPXVQNOHP-UHFFFAOYSA-N 0.000 description 5
- 229960004884 fluconazole Drugs 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 4
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 230000001580 bacterial effect Effects 0.000 description 4
- 238000013461 design Methods 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
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- 241000675278 Candida albicans SC5314 Species 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
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- 238000012423 maintenance Methods 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- -1 piperazine compound Chemical class 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- BBDTVGAGSDPVHT-UHFFFAOYSA-N 2-phenylmethoxyoxirane Chemical compound C=1C=CC=CC=1COC1CO1 BBDTVGAGSDPVHT-UHFFFAOYSA-N 0.000 description 2
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 2
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- 208000031888 Mycoses Diseases 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/095—Sulfur, selenium, or tellurium compounds, e.g. thiols
- A61K31/10—Sulfides; Sulfoxides; Sulfones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
本发明公开了一种抗白色念珠菌化合物及其制备方法和应用。所述抗白色念珠菌化合物的结构式如式(I)所示：其中，R1为H或苯基，R2为H或CH2CH3。该化合物对白色念珠菌的粘附性、菌丝形成和致病性具有很好的抑制作用。而且，该化合物本身毒性较小，不影响人类细胞的生长，不易产生耐药性，在新型抗真菌药物的开发，尤其是抗白色念珠菌感染药物的开发方面具有很好的应用前景。
Description
PCT国内申请，说明书已公开。
Claims (9)
- PCT国内申请，权利要求书已公开。
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/CN2017/105399 WO2019071394A1 (zh) | 2017-10-09 | 2017-10-09 | 一种抗白色念珠菌的新型化合物及其制备方法和应用 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN109803656A true CN109803656A (zh) | 2019-05-24 |
| CN109803656B CN109803656B (zh) | 2021-08-31 |
Family
ID=66100347
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201780025353.9A Active CN109803656B (zh) | 2017-10-09 | 2017-10-09 | 一种抗白色念珠菌的化合物及其制备方法和应用 |
Country Status (2)
| Country | Link |
|---|---|
| CN (1) | CN109803656B (zh) |
| WO (1) | WO2019071394A1 (zh) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102762207A (zh) * | 2008-05-09 | 2012-10-31 | 爱莫里大学 | 用于治疗神经精神疾患的nmda受体拮抗剂 |
-
2017
- 2017-10-09 CN CN201780025353.9A patent/CN109803656B/zh active Active
- 2017-10-09 WO PCT/CN2017/105399 patent/WO2019071394A1/zh active Application Filing
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102762207A (zh) * | 2008-05-09 | 2012-10-31 | 爱莫里大学 | 用于治疗神经精神疾患的nmda受体拮抗剂 |
Non-Patent Citations (3)
| Title |
|---|
| BAHIDJA CHERFAOUI ET AL.: "Synthesis and evaluation of 4-(2-hydroxypropyl)piperazin-1-yl) derivatives as Hsp90 inhibitors", 《BIOORGANIC & MEDICINAL CHEMISTRY》 * |
| R.C.GUPTA ET AL.: "3-Tertiary amino-1-aryloxy- or aryl-propanes and -propan-2-ols and some related compounds", 《ARZNEIM.-FORSCH./DRUG RES.》 * |
| S. T. V. S. KIRAN KUMAR ET AL.: "Synthesis of benzenepropanamine analogues as non-detergent spermicides with antitrichomonas and anticandida activities", 《BIOORGANIC & MEDICINAL CHEMISTRY》 * |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2019071394A1 (zh) | 2019-04-18 |
| CN109803656B (zh) | 2021-08-31 |
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