10601-99-7

Basic information

• Product Name: 3-ETHYNYL-BENZOIC ACID
• Synonyms: 3-ETHYNYL-BENZOIC ACID;Benzoic acid, 3-ethynyl- (9CI);3-ethynylbenzoic acid(SALTDATA: FREE);3-Ethynylbenzoic acid 95%;3-Eethynylbenzoic acid
• CAS NO: 10601-99-7
• Molecular Formula: C₉H₆O₂
• Molecular Weight: 146.14
• Mol File: 10601-99-7.mol

Chemical Properties

• Melting Point: 164-171°C
• Boiling Point: 300.151 °C at 760 mmHg
• Flash Point: 135.584 °C
• Appearance: /
• Density: 1.233 g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.592
• Storage Temp.: 2-8°C
• PKA: 3.99±0.10(Predicted)
• CAS DataBase Reference: 3-ETHYNYL-BENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-ETHYNYL-BENZOIC ACID(10601-99-7)
• EPA Substance Registry System: 3-ETHYNYL-BENZOIC ACID(10601-99-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36-43
• Safety Statements: 26-36/37/39
• WGK Germany: nwg
• Hazardous Substances Data: 10601-99-7(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
3-Ethynyl-benzoic acid serves as a versatile building block in organic synthesis, contributing to the production of a wide range of chemical compounds. Its unique structure allows for various chemical reactions, making it a valuable component in the synthesis of complex organic molecules.
Used as a Precursor in Pharmaceutical Synthesis:
In the pharmaceutical industry, 3-ethynyl-benzoic acid is utilized as a precursor for the synthesis of various drugs. Its ethynyl group can be further modified or used as a starting point for the creation of new pharmaceutical compounds, potentially leading to the development of novel treatments and medications.
Used as a Precursor in Agrochemical Synthesis:
3-Ethynyl-benzoic acid also plays a role in the agrochemical sector, where it is employed as a precursor for the synthesis of various agrochemicals. Its unique properties enable the development of new compounds that can be used in agriculture to improve crop protection and yield.
Used in Dye Production:
In the dye industry, 3-ethynyl-benzoic acid is used as a starting material for the synthesis of different types of dyes. Its chemical structure allows for the creation of dyes with specific color properties, making it an important component in the production of various colorants for textiles, plastics, and other applications.

InChI:InChI=1/C9H6O2/c1-2-7-4-3-5-8(6-7)9(10)11/h1,3-6H,(H,10,11)

Upstream product

• 10602-06-9 methyl 3-ethynylbenzoate 
• 870245-85-5 3-Carboxyethynyl-benzoic acid 
• 618-51-9 3-Iodobenzoic acid 
• 618-91-7 methyl 3-iodo-benzoate 
• 77123-59-2 methyl 3-<(trimethylsilyl)ethynyl>benzoate 
• 618-89-3 methyl 3-bromobenzoate 
• 150969-58-7 ethyl 3-<(trimethylsilyl)ethynyl>benzoate 
• 24398-88-7 ethyl 3-bromobenzoate 

Downstream Products

• 375853-73-9 N,N-bis-(tert-butoxycarbonyl)-3-[1-(3-ethynyl-benzoyl)-piperidin-4-yl]-benzylamine 
• 1025053-27-3 C₁₈H₁₁F₃N₂O₂ 
• 1027730-01-3 N-(2,5-dimethyl-2H-pyrazol-3-yl)-3-ethynyl-benzamide 
• 143587-37-5 3-ethynylbenzoyl chloride 
• 1138342-06-9 zinc(II) 5,10,15,20-tetrakis(3,5-di-tert-butylphenyl)-2-(3-carboxyphenylethynyl)porphyrin 
• 1198118-78-3 3-[4-(thiophene-3-carbonyl)naphthalen-2-yl]-benzoic acid 
• 1206102-98-8 3-(1-(4-isopropylphenyl)-1H-1,2,3-triazol-4-yl)benzoic acid 

Relevant articles and documents

Design, synthesis, and biological evaluations of novel 3-amino-4-ethynyl indazole derivatives as Bcr-Abl kinase inhibitors with potent cellular antileukemic activity

Breakpoint cluster region-Abelson (Bcr-Abl) kinase is a key driver in the pathophysiology of chronic myelogenous leukemia (CML). Broadening the chemical diversity of Bcr-Abl kinase inhibitors with novel chemical entities possessing favorable target potency and cellular efficacy is a current medical demand for CML treatment. In this respect, a new series of ethynyl bearing 3-aminoindazole based Bcr-Abl inhibitors has been designed, synthesized, and biologically evaluated. The target compounds were designed based on introducing the key structural features of ponatinib, alkyne spacer and diarylamide, into the previously reported indazole II to improve its Bcr-Abl inhibitory activity and overcome its poor cellular potency. All target compounds elicited potent activity against Bcr-AblWT with sub-micromolar IC50 values ranging 4.6–667 nM. In addition, certain derivatives exhibited promising potency over the clinically imatinib-resistant Bcr-AblT315I. Among the target molecules, compounds 9c, 9h and 10c stood as the most potent derivatives with IC50 values of 15.4 nM, 4.6 nM, and 25.8 nM, respectively, against Bcr-AblWT. Interestingly, 9h showed 2 folds and 3.6 times superior potency to the lead indazole II and 10c, respectively, against Bcr-AblT315I. Molecular docking of 9h pointed out its possibility to be a type II kinase inhibitor. Furthermore, all compounds, except 9b, showed highly potent antiproliferative activity against the Bcr-Abl positive leukemia K562 cell (MTT assay) surpassing the modest activity of lead indazole II. Moreover, the most potent members 9h and 10c exerted potent antileukemic activity against NCI leukemia panel, particularly K562 cell (SRB assay) with GI50 less than 10 nM, being superior to the FDA approved drug imatinib. Further biochemical hERG and cellular toxicity, phosphorylation assay, and NanoBRET target engagement of 9h underscored its merits as a promising candidate for CML therapy.

NOVEL INDAZOLE DERIVATIVES AND PHARMACEUTICAL COMPOSITION FOR PREVENTING, ALLEVIATING OR TREATING CANCER CONTAINING THE SAME

Disclosed are a compound selected from novel indazole derivatives, pharmaceutically acceptable salts thereof, hydrates thereof and stereoisomers thereof, a method for preparing the compound, and a pharmaceutical composition for preventing, alleviating or treating cancer containing the compound as an active ingredient. The novel indazole derivatives exhibit excellent ABL/DDR1 inhibitory efficacy and anti-proliferative efficacy against cancer cells, specifically blood cancer cells, and inhibitory activity against ABL T315I point mutations, thus being useful for the prevention, alleviation or treatment of cancer, specifically blood cancer, especially chronic myelogenous leukemia.

BTK Inhibitors and uses thereof

The invention discloses a bruton's tyrosine kinase (BTK) inhibitor and use thereof. Specifically, the invention provides heteroaromatic compounds or stereoisomers, geometrical isomers, tautomers, racemates, nitrogen oxides, hydrates, solvates, metabolites and pharmaceutically acceptable salts or prodrugs thereof, and pharmaceutical compositions containing the heteroaromatic compounds; the invention also discloses use of the heteroaromatic compounds or the pharmaceutical compositions containing the heteroaromatic compounds in preparation of medicines; the medicines can be used for treating autoimmune diseases, inflammatory diseases or proliferative diseases.

Using the same hydroxamic acid derivative and HDAC8 inhibitor (by machine translation)

Disclosed are: a compound which is capable of inhibiting the function of HDAC8; and an HDAC8 inhibitor. Specifically disclosed is a hydroxamic acid derivative which is characterized by being composed of a compound represented by general formula (1) (wherein X represents an aromatic substituent or an optionally substituted 3-8 membered ring, and n represents an integer of 0-20), or a pharmaceutically acceptable salt, hydrate, solvate or prodrug thereof.

Development of Alkyne-Containing Pyrazolopyrimidines to Overcome Drug Resistance of Bcr-Abl Kinase

Despite the success of imatinib at inhibiting Bcr-Abl and treating chronic myelogenous leukemia (CML), resistance to the therapy occurs over time in patients. In particular, the resistance to imatinib caused by the gatekeeper mutation T315I in Bcr-Abl remains a challenge in the clinic. Inspired by the successful development of ponatinib to curb drug resistance, we hypothesize that the incorporation of an alkyne linker in other heterocyclic scaffolds can also achieve potent inhibition of Bcr-AblT315I by allowing for simultaneous occupancy of both the active site and the allosteric pocket in the Abl kinase domain. Herein, we describe the design, synthesis, and characterization of a series of alkyne-containing pyrazolopyrimidines as Bcr-Abl inhibitors. Our results demonstrate that some alkyne-containing pyrazolopyrimidines potently inhibit not only AblT315I in vitro but also Bcr-AblT315I in cells. These pyrazolopyrimidines can serve as lead compounds for future development of novel targeted therapy to overcome drug resistance of CML.

Design, Synthesis, and Evaluation of Triazole Derivatives That Induce Nrf2 Dependent Gene Products and Inhibit the Keap1-Nrf2 Protein-Protein Interaction

The transcription factor Nrf2 regulates the expression of a large network of cytoprotective and metabolic enzymes and proteins. Compounds that directly and reversibly inhibit the interaction between Nrf2 and its main negative regulator Keap1 are potential pharmacological agents for a range of disease types including neurodegenerative conditions and cancer. We describe the development of a series of 1,4-diphenyl-1,2,3-triazole compounds that inhibit the Nrf2-Keap1 protein-protein interaction (PPI) in vitro and in live cells and up-regulate the expression of Nrf2-dependent gene products.

DIHYDROPYRIDO PYRIMIDINE COMPOUNDS AS AUTOTAXIN INHIBITORS

The present invention provides compounds of the formula (I) or a pharmaceutically acceptable salt thereof. Compounds of the invention are autotaxin inhibitors useful in the treatment of pain associated with osteoarthritis.

Rapid discovery of highly potent and selective inhibitors of histone deacetylase 8 using click chemistry to generate candidate libraries

To find HDAC8-selective inhibitors, we designed a library of HDAC inhibitor candidates, each containing a zinc-binding group that coordinates with the active-site zinc ion, linked via a triazole moiety to a capping structure that interacts with residues on the rim of the active site. These compounds were synthesized by using click chemistry. Screening identified HDAC8-selective inhibitors including C149 (IC50 = 0.070 μM), which was more potent than PCI-34058 (6) (IC50 = 0.31 μM), a known HDAC8 inhibitor. Molecular modeling suggested that the phenylthiomethyl group of C149 binds to a unique hydrophobic pocket of HDAC8, and the orientation of the phenylthiomethyl and hydroxamate moieties (fixed by the triazole moiety) is important for the potency and selectivity. The inhibitors caused selective acetylation of cohesin in cells and exerted growth-inhibitory effects on T-cell lymphoma and neuroblastoma cells (GI50 = 3-80 μM). These findings suggest that HDAC8-selective inhibitors have potential as anticancer agents.