Methyl 5-ethynylpyridine-2-carboxylate
- CAS Number:17880-61-4
- Molecular Formula:C9H7NO2
- Molecular Weight:161.16
- Mol File:17880-61-4.mol
Synonyms:Methyl 5-ethynylpyridine-2-carboxylate;Methyl 5-ethynylpicolinate, 5-Ethynyl-2-(methoxycarbonyl)pyridine;Methyl 5-ethynylpicolinate
Physicochemical Properties
- Melting Point:N/A
- Boiling Point:N/A
- Density:N/A
- Solubility:N/A
- Flash Point:N/A
- Vapor Density:N/A
- Refractive Index:N/A
- Sensitive:N/A
- Storage Temp.:N/A
- Appearance/Colour:N/A
Methyl 5-ethynylpyridine-2-carboxylate Safety information and MSDS
·Hazard identification:
| Pictogram(s) | no data available |
|---|---|
| Signal word | no data available |
| Hazard statement(s) | no data available |
| Precautionary statement(s) | |
| Prevention | no data available |
| Response | no data available |
| Storage | no data available |
| Disposal | no data available |
·Composition/information on ingredients:
| Chemical name | Common names and synonyms | CAS number | EC number | Concentration |
|---|---|---|---|---|
| methyl 5-ethynylpyridine-2-carboxylate | methyl 5-ethynylpyridine-2-carboxylate | 17880-61-4 | none | 100% |
·First-aid measures:
General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
·Fire-fighting measures:
Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.
·Accidental release measures:
Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.
Methyl 5-ethynylpyridine-2-carboxylate Relevant articles
All total 9 Articles be found
All total 9 Articles be foundETHYNYLBENZENE DERIVATIVES
-
Page/Page column 124, (2012/03/26)
Disclosed are compounds of formulae (I), (II), and (II)I: and pharmaceutically acceptable salts thereof, wherein the variables, R, R1, R2, R3, R101, L, D, Q, Y, X, and Z are defined herein. These compounds are useful for treating Gram-negative bacteria infections.
DISUBSTITUTED ALKYNE DERIVATIVES
-
Page/Page column 121-122; 165-166, (2020/07/14)
The present invention relates to disubstituted alkyne derivatives. These compounds are useful for the prevention and/or treatment of several medical conditions including hyperproliferative disorders and diseases.
Design, synthesis and structure-activity relationship evaluation of novel LpxC inhibitors as Gram-negative antibacterial agents
Ding, Shi,Dai, Rui-Yang,Wang, Wen-Ke,Cao, Qiao,Lan, Le-Fu,Zhou, Xian-Li,Yang, Yu-She
supporting information, p. 94 - 102 (2017/12/15)
LpxC inhibitors are new-type antibacterial agents developed in the last twenty years, mainly against Gram-negative bacteria infections. To develop novel LpxC inhibitors with good antibacterial activities and biological metabolism, we summarized the basic skeleton of reported LpxC inhibitors, designed and synthesized several series of compounds and tested their antibacterial activities against Escherichial coli and Pseudomonas aeruginosa in vitro. Structure-activity relationships have been discussed in this article. The metabolism stability of YDL-2, YDL-5, YDL-8, YDL-14, YDL-20–YDL-23 have been evaluated in liver microsomes, which indicated that the 2-amino isopropyl group may be a preferred structure than the 2-hydroxy ethyl group in the design of LpxC inhibitors.
Design, biological evaluation and X-ray crystallography of nanomolar multifunctional ligands targeting simultaneously acetylcholinesterase and glycogen synthase kinase-3
Oukoloff, Killian,Coquelle, Nicolas,Bartolini, Manuela,Naldi, Marina,Le Guevel, Rémy,Bach, Stéphane,Josselin, Béatrice,Ruchaud, Sandrine,Catto, Marco,Pisani, Leonardo,Denora, Nunzio,Iacobazzi, Rosa Maria,Silman, Israel,Sussman, Joel L.,Buron, Frédéric,Colletier, Jacques-Philippe,Jean, Ludovic,Routier, Sylvain,Renard, Pierre-Yves
, p. 58 - 77 (2019/02/25)
Both cholinesterases (AChE and BChE) and kinases, such as GSK-3α/β, are associated with the pathology of Alzheimer's disease. Two scaffolds, targeting AChE (tacrine) and GSK-3α/β (valmerin) simultaneously, were assembled, using copper(I)-catalysed azide alkyne cycloaddition (CuAAC), to generate a new series of multifunctional ligands. A series of eight multi-target directed ligands (MTDLs) was synthesized and evaluated in vitro and in cell cultures. Molecular docking studies, together with the crystal structures of three MTDL/TcAChE complexes, with three tacrine-valmerin hybrids allowed designing an appropriate linker containing a 1,2,3-triazole moiety whose incorporation preserved, and even increased, the original inhibitory potencies of the two selected pharmacophores toward the two targets. Most of the new derivatives exhibited nanomolar affinity for both targets, and the most potent compound of the series displayed inhibitory potencies of 9.5 nM for human acetylcholinesterase (hAChE) and 7 nM for GSK-3α/β. These novel dual MTDLs may serve as suitable leads for further development, since, in the micromolar range, they exhibited low cytotoxicity on a panel of representative human cell lines including the human neuroblastoma cell line SH-SY5Y. Moreover, these tacrine-valmerin hybrids displayed a good ability to penetrate the blood-brain barrier (BBB) without interacting with efflux pumps such as P-gp.
COMBINATION PRODUCT FOR THE TREATMENT OF CANCEROUS DISEASES
-
Page/Page column 128; 172, (2021/12/31)
The present invention relates to a product for combination therapies useful for the treatment of cancer diseases. In particular, the invention relates to the combination of an anti-PD-Ll antibody and an MCT4 inhibitor of Formula (I). The therapeutic combination may be utilized for the use in treating a subject having a cancer disease that tests positive for PD-L1 and/or MCT4 expression.
Methyl 5-ethynylpyridine-2-carboxylate Synthetic route And Reaction conditions
- 29682-15-3
methyl 5-bromopicolinate
- 17880-61-4
methyl 5-ethynylpyridine-2-carboxylate
| Conditions | Yield |
|---|---|
Multi-step reaction with 2 steps 1: copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; triethylamine / tetrahydrofuran / 18 h / 60 °C / Inert atmosphere 2: potassium fluoride / methanol; dichloromethane / 2 h / 20 °C Withpotassium fluoride;
copper(l) iodide;
trans-bis(triphenylphosphine)palladium dichloride;
triethylamine;Intetrahydrofuran;
methanol;
dichloromethane;1: Sonogashira-Hagihara reaction; | |
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 14 h / 70 °C / Sealed vessel; Inert atmosphere 2: potassium carbonate; methanol / 0.67 h / 20 °C / Inert atmosphere | |
Multi-step reaction with 2 steps 1: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / tetrahydrofuran / 5 h / 60 °C 2: potassium carbonate / 1 h / 20 °C / Inert atmosphere Withbis-triphenylphosphine-palladium(II) chloride;
copper(l) iodide;
potassium carbonate;
triethylamine;Intetrahydrofuran;1: |Sonogashira Cross-Coupling; | |
Multi-step reaction with 2 steps 1: triethylamine; trans-bis(triphenylphosphine)palladium dichloride; copper(l) iodide / tetrahydrofuran / 5 h / 60 °C / Inert atmosphere 2: potassium fluoride / methanol; dichloromethane / 12 h / 20 °C Withpotassium fluoride;
copper(l) iodide;
trans-bis(triphenylphosphine)palladium dichloride;
triethylamine;Intetrahydrofuran;
methanol;
dichloromethane;1: |Sonogashira Cross-Coupling; | |
Multi-step reaction with 2 steps 1: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / tetrahydrofuran / 50 °C / Inert atmosphere 2: potassium carbonate; methanol / 0.25 h / 20 °C / Inert atmosphere |
- 30766-11-1
5-bromoisonicotinic acid
- 17880-61-4
methyl 5-ethynylpyridine-2-carboxylate
| Conditions | Yield |
|---|---|
Multi-step reaction with 3 steps 1: benzene; methanol / 1 h / 20 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine / copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 14 h / 70 °C / Sealed vessel; Inert atmosphere 3: potassium carbonate; methanol / 0.67 h / 20 °C / Inert atmosphere |
- 17880-61-4
methyl 5-ethynylpyridine-2-carboxylate
| Conditions | Yield |
|---|---|
| 90% | |
Withmethanol;
potassium carbonate;
at 20 ℃;
for 0.25h;
Reagent/catalyst;
Inert atmosphere; | 85.5% |
| 85.5% | |
| 85.5% | |
Withmethanol;
potassium carbonate;
at 20 ℃;
for 0.666667h;
Inert atmosphere; | 84% |
| 77% | |
Withpotassium carbonate;
at 20 ℃;
for 1h;
Inert atmosphere; |
- 217966-72-8
4-(tert-butyl)-2-iodophenyltrifluoromethane sulfonate
- 17880-61-4
methyl 5-ethynylpyridine-2-carboxylate
- 1350553-45-5
methyl 5-((5-tert-butyl-2-(trifluoromethylsulfonyloxy)phenyl)ethynyl)picolinate
| Conditions | Yield |
|---|---|
Withcopper(l) iodide;
trans-bis(triphenylphosphine)palladium dichloride;
triethylamine;Intetrahydrofuran;at 20 ℃;
for 18h;
Inert atmosphere; | 86% |
- 17880-61-4
methyl 5-ethynylpyridine-2-carboxylate
- 1350553-48-8
methyl 5-((5-tert-butyl-2-((triisopropylsilyl)ethynyl)phenyl)ethynyl)picolinate
| Conditions | Yield |
|---|---|
Multi-step reaction with 2 steps 1: copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; triethylamine / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere 2: copper(l) iodide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; diisopropylamine / N,N-dimethyl-formamide / 48 h / 70 °C / Inert atmosphere Withcopper(l) iodide;
dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2;
trans-bis(triphenylphosphine)palladium dichloride;
triethylamine;
diisopropylamine;Intetrahydrofuran;
N,N-dimethyl-formamide;1: Sonogashira-Hagihara reaction; |
- 17880-61-4
methyl 5-ethynylpyridine-2-carboxylate
- 1350553-51-3
methyl 5-((5-tert-butyl-2-ethynylphenyl)ethynyl)picolinate
| Conditions | Yield |
|---|---|
Multi-step reaction with 3 steps 1: copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; triethylamine / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere 2: copper(l) iodide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; diisopropylamine / N,N-dimethyl-formamide / 48 h / 70 °C / Inert atmosphere 3: tetrabutyl ammonium fluoride / tetrahydrofuran; water / 3 h / 20 °C |
- 17880-61-4
methyl 5-ethynylpyridine-2-carboxylate
- 1350553-54-6
dimethyl 5,5'-(6,6'-(buta-1,3-diyne-1,4-diyl)bis(3-tert-butyl-6,1-phenylene)bis(ethyne-2,1-diyl))dipicolinate
| Conditions | Yield |
|---|---|
Multi-step reaction with 4 steps 1: copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; triethylamine / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere 2: copper(l) iodide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; diisopropylamine / N,N-dimethyl-formamide / 48 h / 70 °C / Inert atmosphere 3: tetrabutyl ammonium fluoride / tetrahydrofuran; water / 3 h / 20 °C 4: pyridine; trans-bis(triphenylphosphine)palladium dichloride; iodine; copper diacetate; diisopropylamine / tetrahydrofuran / 2 h / 20 °C Withpyridine;
copper(l) iodide;
dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2;
trans-bis(triphenylphosphine)palladium dichloride;
tetrabutyl ammonium fluoride;
iodine;
copper diacetate;
triethylamine;
diisopropylamine;Intetrahydrofuran;
water;
N,N-dimethyl-formamide;1: Sonogashira-Hagihara reaction; |
- 17880-61-4
methyl 5-ethynylpyridine-2-carboxylate
- 1350553-57-9
5,5'-(6,6'-(buta-1,3-diyne-1,4-diyl)bis(3-tert-butyl-6,1-phenylene)bis(ethyne-2,1-diyl))dipicolinic acid
| Conditions | Yield |
|---|---|
Multi-step reaction with 5 steps 1: copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; triethylamine / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere 2: copper(l) iodide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; diisopropylamine / N,N-dimethyl-formamide / 48 h / 70 °C / Inert atmosphere 3: tetrabutyl ammonium fluoride / tetrahydrofuran; water / 3 h / 20 °C 4: pyridine; trans-bis(triphenylphosphine)palladium dichloride; iodine; copper diacetate; diisopropylamine / tetrahydrofuran / 2 h / 20 °C 5: methanol; sodium hydroxide / dichloromethane / 3 h / 40 °C Withpyridine;
methanol;
copper(l) iodide;
dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2;
trans-bis(triphenylphosphine)palladium dichloride;
tetrabutyl ammonium fluoride;
iodine;
copper diacetate;
triethylamine;
diisopropylamine;
sodium hydroxide;Intetrahydrofuran;
dichloromethane;
water;
N,N-dimethyl-formamide;1: Sonogashira-Hagihara reaction; |
- 17880-61-4
methyl 5-ethynylpyridine-2-carboxylate
| Conditions | Yield |
|---|---|
Multi-step reaction with 2 steps 1: pyridine / copper diacetate / methanol / 20 h / 20 °C / Inert atmosphere 2: sodium hydroxide; methanol / 0.67 h / 20 °C / Reflux; Inert atmosphere |
- 17880-61-4
methyl 5-ethynylpyridine-2-carboxylate
- 29682-15-3
methyl 5-bromopicolinate
| Conditions | Yield |
|---|---|
Withtetrakis(triphenylphosphine) palladium(0);
triethylamine;Intetrahydrofuran;at 75 ℃;
for 41h;
Schlenk technique; | 80% |
Methyl 5-ethynylpyridine-2-carboxylate Raw materials
Methyl 5-ethynylpyridine-2-carboxylate Target Products
- 1350553-45-5
methyl 5-((5-tert-butyl-2-(trifluoromethylsulfonyloxy)phenyl)ethynyl)picolinate
- 1350553-48-8
methyl 5-((5-tert-butyl-2-((triisopropylsilyl)ethynyl)phenyl)ethynyl)picolinate
- 1350553-51-3
methyl 5-((5-tert-butyl-2-ethynylphenyl)ethynyl)picolinate
- 1350553-54-6
dimethyl 5,5'-(6,6'-(buta-1,3-diyne-1,4-diyl)bis(3-tert-butyl-6,1-phenylene)bis(ethyne-2,1-diyl))dipicolinate
- 1350553-57-9
5,5'-(6,6'-(buta-1,3-diyne-1,4-diyl)bis(3-tert-butyl-6,1-phenylene)bis(ethyne-2,1-diyl))dipicolinic acid
Business Type:
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Country :
China (Mainland)(7)
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