CN102617562B - 一种噻唑衍生物及其制备方法与用途 - Google Patents
一种噻唑衍生物及其制备方法与用途 Download PDFInfo
- Publication number
- CN102617562B CN102617562B CN201210085912.4A CN201210085912A CN102617562B CN 102617562 B CN102617562 B CN 102617562B CN 201210085912 A CN201210085912 A CN 201210085912A CN 102617562 B CN102617562 B CN 102617562B
- Authority
- CN
- China
- Prior art keywords
- thiazole derivative
- preparation
- thiazole
- derivative according
- product
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 241001597008 Nomeidae Species 0.000 title abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000002904 solvent Substances 0.000 claims abstract description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims abstract description 5
- 150000007979 thiazole derivatives Chemical class 0.000 claims description 24
- 238000006555 catalytic reaction Methods 0.000 claims description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- 239000003480 eluent Substances 0.000 claims description 5
- 238000010828 elution Methods 0.000 claims description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- 230000000844 anti-bacterial effect Effects 0.000 claims description 4
- 229940088710 antibiotic agent Drugs 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000010908 decantation Methods 0.000 claims description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 239000000741 silica gel Substances 0.000 claims description 2
- 229910002027 silica gel Inorganic materials 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 11
- 238000006243 chemical reaction Methods 0.000 abstract description 5
- 230000003115 biocidal effect Effects 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 238000005481 NMR spectroscopy Methods 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 6
- 235000015097 nutrients Nutrition 0.000 description 6
- 241000589540 Pseudomonas fluorescens Species 0.000 description 5
- 230000000845 anti-microbial effect Effects 0.000 description 5
- 238000004321 preservation Methods 0.000 description 5
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 4
- 239000012980 RPMI-1640 medium Substances 0.000 description 4
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- OBSLLHNATPQFMJ-UHFFFAOYSA-N 2,4-Dimethylthiazole Chemical compound CC1=CSC(C)=N1 OBSLLHNATPQFMJ-UHFFFAOYSA-N 0.000 description 3
- 241000193830 Bacillus <bacterium> Species 0.000 description 3
- 244000063299 Bacillus subtilis Species 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 241000191967 Staphylococcus aureus Species 0.000 description 3
- 210000001072 colon Anatomy 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 2
- 235000014469 Bacillus subtilis Nutrition 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 102000038030 PI3Ks Human genes 0.000 description 2
- 108091007960 PI3Ks Proteins 0.000 description 2
- 239000001888 Peptone Substances 0.000 description 2
- 108010080698 Peptones Proteins 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000006254 arylation reaction Methods 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 229960001192 bekanamycin Drugs 0.000 description 2
- 229960005091 chloramphenicol Drugs 0.000 description 2
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 description 2
- SKKLOUVUUNMCJE-FQSMHNGLSA-N kanamycin B Chemical compound N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SKKLOUVUUNMCJE-FQSMHNGLSA-N 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- 239000013642 negative control Substances 0.000 description 2
- 229940056360 penicillin g Drugs 0.000 description 2
- 235000019319 peptone Nutrition 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 150000003557 thiazoles Chemical class 0.000 description 2
- MKEJZKKVVUZXIS-UHFFFAOYSA-N 2,4-dibromo-1,3-thiazole Chemical class BrC1=CSC(Br)=N1 MKEJZKKVVUZXIS-UHFFFAOYSA-N 0.000 description 1
- ZGWGSEUMABQEMD-UHFFFAOYSA-N 4-methyl-1,3-thiazole-5-carboxylic acid Chemical compound CC=1N=CSC=1C(O)=O ZGWGSEUMABQEMD-UHFFFAOYSA-N 0.000 description 1
- DNHKSCAYDWTXHD-UHFFFAOYSA-N 4-methyl-5-phenyl-1,3-thiazole Chemical compound N1=CSC(C=2C=CC=CC=2)=C1C DNHKSCAYDWTXHD-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 239000012981 Hank's balanced salt solution Substances 0.000 description 1
- 238000007341 Heck reaction Methods 0.000 description 1
- 241000725303 Human immunodeficiency virus Species 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 239000007993 MOPS buffer Substances 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 238000006619 Stille reaction Methods 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 102000013530 TOR Serine-Threonine Kinases Human genes 0.000 description 1
- 108010065917 TOR Serine-Threonine Kinases Proteins 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004820 blood count Methods 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000006880 cross-coupling reaction Methods 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000013100 final test Methods 0.000 description 1
- 108700012707 hepatitis C virus NS3 Proteins 0.000 description 1
- -1 heteroaryl carboxylic acid compound Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 229930182824 kanamycin B Natural products 0.000 description 1
- SKKLOUVUUNMCJE-UHFFFAOYSA-N kanendomycin Natural products NC1C(O)C(O)C(CN)OC1OC1C(O)C(OC2C(C(N)C(O)C(CO)O2)O)C(N)CC1N SKKLOUVUUNMCJE-UHFFFAOYSA-N 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 239000006166 lysate Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 238000007146 photocatalysis Methods 0.000 description 1
- 229940121649 protein inhibitor Drugs 0.000 description 1
- 239000012268 protein inhibitor Substances 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910021654 trace metal Inorganic materials 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
Images
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (8)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201210085912.4A CN102617562B (zh) | 2012-03-28 | 2012-03-28 | 一种噻唑衍生物及其制备方法与用途 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201210085912.4A CN102617562B (zh) | 2012-03-28 | 2012-03-28 | 一种噻唑衍生物及其制备方法与用途 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN102617562A CN102617562A (zh) | 2012-08-01 |
CN102617562B true CN102617562B (zh) | 2014-01-15 |
Family
ID=46557820
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201210085912.4A Expired - Fee Related CN102617562B (zh) | 2012-03-28 | 2012-03-28 | 一种噻唑衍生物及其制备方法与用途 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN102617562B (zh) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN116813608B (zh) * | 2023-06-08 | 2024-03-22 | 英矽智能科技(上海)有限公司 | 噻唑类化合物及其应用 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101654455A (zh) * | 2009-09-24 | 2010-02-24 | 绍兴文理学院 | 吡咯[1,2-a]咪唑类化合物及其制备方法和抗肿瘤应用 |
CN101654459A (zh) * | 2009-09-24 | 2010-02-24 | 绍兴文理学院 | 吡咯[2,1-b]噻唑类化合物及其制备方法和抗肿瘤应用 |
-
2012
- 2012-03-28 CN CN201210085912.4A patent/CN102617562B/zh not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
CN102617562A (zh) | 2012-08-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN108191854A (zh) | 1-(n-环丙沙星酰胺基)-6-氟-7-哌嗪-萘啶酮酸化合物及其制备方法和应用 | |
CN103333148A (zh) | 3,3′-(3,4-二氯苯亚甲基)-双-4-羟基香豆素及其在制备抗多重耐药细菌药物中的应用 | |
Xie et al. | A dual-caged resorufin probe for rapid screening of infections resistant to lactam antibiotics | |
CN102617562B (zh) | 一种噻唑衍生物及其制备方法与用途 | |
CN107501073A (zh) | 樱草素衍生物及其合成方法和应用 | |
CN109970644A (zh) | 一种检测溶酶体极性的双光子荧光探针及其制备方法和应用 | |
CN106146395B (zh) | 3-羟基吡啶化合物、其制备方法及其制药用途 | |
CN105622492B (zh) | 具有抗耐药菌活性的查尔酮衍生物 | |
CN114605334B (zh) | 一种2-氨基嘧啶类化合物、制备方法、应用及生物膜抑制剂 | |
CN104530082B (zh) | 头孢硫脒化合物 | |
CN103193770B (zh) | 取代苯并噻唑类抗真菌化合物及其制备方法与应用 | |
CN110041306B (zh) | 4-羟基-2-喹诺酮-氮-(4-喹唑啉酮)-3-甲酰胺类衍生物 | |
CN114507158A (zh) | 一类具有抗耐药菌活性的截短侧耳素α-氰基肉桂酸酯类化合物及其制备方法与应用 | |
CN104059011B (zh) | 一种取代吡咯衍生物及其制备方法和应用 | |
CN112824397B (zh) | 一种洛美沙星的丙烯酮衍生物及其制备方法和应用 | |
CN104961707B (zh) | 取代噻唑酮类分泌型天冬氨酸蛋白酶抑制剂及其制备方法 | |
CN113372296A (zh) | 用于抑制多重耐药的金黄色葡萄球菌的硒啉类化合物及用途 | |
CN106397459B (zh) | 硫代二酮哌嗪类化合物及其应用 | |
CN105497004B (zh) | 呫吨酮二聚体类化合物IUE-1799a的用途 | |
CN104910177B (zh) | 一种氨甲基三唑取代的三环氟喹诺酮羧酸类衍生物及其制备方法和应用 | |
CN102603867A (zh) | 多氧霉素与尼可霉素杂合抗生素及其制备方法 | |
AU2013291546B2 (en) | A furanone containing polymer compound with bacteria-adhesion properties | |
CN114539241B (zh) | 一种含噻唑-吡啶甲基芳杂环季铵盐侧链的截短侧耳素衍生物及其制备方法与应用 | |
CN110054579A (zh) | 一种4-(1-h吲哚)苯酚衍生物的制备方法及其应用 | |
CN104974152A (zh) | 一种取代四氢喹啉衍生物及其水解产物与其合成方法和应用 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
ASS | Succession or assignment of patent right |
Owner name: ZHEJIANG DAMEI BIO-TECHNOLOGY CO., LTD. Free format text: FORMER OWNER: SHAOXING UNIVERSITY Effective date: 20150526 |
|
C41 | Transfer of patent application or patent right or utility model | ||
TR01 | Transfer of patent right |
Effective date of registration: 20150526 Address after: 312000 Zhejiang city of Shaoxing province Cao Jiang Lu No. 4 Building 5 Patentee after: ZHEJIANG DELTA BIOLOGICAL TECHNOLOGY CO.,LTD. Address before: 312000 Zhejiang Province, Shaoxing City Ring Road No. 508 more Patentee before: Shaoxing University |
|
CF01 | Termination of patent right due to non-payment of annual fee | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20140115 |