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5398-44-7

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5398-44-7 Usage

Chemical Properties

off-white to beige or light brownish powder

Uses

2,6-Dichloroisonicotinic acid is a derivative of isonicotinic acid (I821760). Treatment of oat cultivars using 2,6-dichloroisonicotinic acid results in an increased accumulation of avenathramide. 2,6-Dichloroisonicotinic acid is a well known inducer of plant resistance and induces the transcription of ZmNAC100 transcription factor.

Definition

ChEBI: A member of the class of pyridines that is isonicotinic acid which is substituted by chlorine at positions 2 and 6.

Check Digit Verification of cas no

The CAS Registry Mumber 5398-44-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,3,9 and 8 respectively; the second part has 2 digits, 4 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 5398-44:
(6*5)+(5*3)+(4*9)+(3*8)+(2*4)+(1*4)=117
117 % 10 = 7
So 5398-44-7 is a valid CAS Registry Number.
InChI:InChI=1/C6H3Cl2NO2/c7-4-1-3(6(10)11)2-5(8)9-4/h1-2H,(H,10,11)/p-1

5398-44-7 Well-known Company Product Price

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  • (Code)Product description
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  • Alfa Aesar

  • (B20541)  2,6-Dichloropyridine-4-carboxylic acid, 98%   

  • 5398-44-7

  • 1g

  • 342.0CNY

  • Detail
  • Alfa Aesar

  • (B20541)  2,6-Dichloropyridine-4-carboxylic acid, 98%   

  • 5398-44-7

  • 5g

  • 1308.0CNY

  • Detail
  • Aldrich

  • (456543)  2,6-Dichloropyridine-4-carboxylicacid  98%

  • 5398-44-7

  • 456543-1G

  • 616.59CNY

  • Detail
  • Aldrich

  • (456543)  2,6-Dichloropyridine-4-carboxylicacid  98%

  • 5398-44-7

  • 456543-5G

  • 2,042.82CNY

  • Detail

5398-44-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 2,6-dichloroisonicotinic acid

1.2 Other means of identification

Product number -
Other names 4-Pyridinecarboxylic acid, 2,6-dichloro-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:5398-44-7 SDS

5398-44-7Relevant articles and documents

Methylsulfanylpyridine based diheteroaryl isocombretastatin analogs as potent anti-proliferative agents

álvarez, Raquel,Aramburu, Laura,Gajate, Consuelo,Vicente-Blázquez, Alba,Mollinedo, Faustino,Medarde, Manuel,Peláez, Rafael

, (2021)

Isocombretastatins are the not isomerizable 1,1-diarylethene isomers of combretastatins. Both families of antimitotics are poorly soluble and new analogs with improved water solubility are needed. The ubiquitous 3,4,5-trimethoxyphenyl ring and most of its replacements contribute to the solubility problem. 39 new compounds belonging to two series of isocombretastatin analogs with 2-chloro-6-methylsulfanyl-4-pyridinyl or 2,6-bis(methylsulfanyl)-4-pyridinyl moieties replacing the 3,4,5-trimethoxyphenyl have been synthesized and their antimitotic activity and aqueous solubility have been studied. We show here that 2-chloro-6-methylsulfanylpyridines are more successful replacements than 2,6-bis(methylsulfanyl)pyridines, giving highly potent tubulin inhibitors and cytotoxic compounds with improved water solubilities. The optimal combination is with indole rings carrying polar substitutions at the three position. The resulting diheteroaryl isocombretastatin analogs showed potent cytotoxic activity against human cancer cell lines caused by tubulin inhibition, as shown by in vitro tubulin polymerization inhibitory assays, cell cycle analysis, and confocal microscopy studies. Cell cycle analysis also showed apoptotic responses following G2/M arrest after treatment. Conformational analysis and docking studies were applied to propose binding modes of the compounds at the colchicine site of tubulin and were in good agreement with the observed SAR. 2-Chloro-6-methylsulfanylpyridines represent a new and successful trimethoxyphenyl ring substitution for the development of improved colchicine site ligands.

Preparation method of 4-amino-2,6-dichloropyridine

-

Paragraph 0108-0110, (2021/03/21)

The invention relates to a preparation method of a halogen-substituted pyridylamine compound, particularly to a preparation method of 4-amino-2,6-dichloropyridine, wherein 2,6-dihydroxy isonicotinic acid is used as a raw material and is subjected to chlorination reaction, Curtius rearrangement or further amine protection group removal to obtain the product. The method has the advantages of accessible raw materials, high yield and low impurity content, avoids the use of explosive reagent sodium azide, and can be further applied to industrial production.

Potent colchicine-site ligands with improved intrinsic solubility by replacement of the 3,4,5-trimethoxyphenyl ring with a 2-methylsulfanyl-6-methoxypyridine ring

Aramburu, Laura,Gajate, Consuelo,Medarde, Manuel,Mollinedo, Faustino,álvarez, Raquel,Peláez, Rafael,Vicente-Blázquez, Alba

, (2020/03/27)

Colchicine site antimitotic agents typically suffer from low aqueous solubilities and are formulated as phosphate prodrugs of phenolic groups. These hydroxyl groups are the aim of metabolic transformations leading to resistance. There is an urgent need for more intrinsically soluble analogues lacking these hydroxyl groups. The 3,4,5-trimethoxyphenyl ring of combretastatin A-4 is a liability in terms of solubility but it is considered essential for high cytotoxic and tubulin polymerization inhibitory (TPI) activity. We have synthesized 36 new analogues of combretastatin A-4 replacing the trimethoxyphenyl moiety with more polar pyridine based moieties, measured their aqueous solubility, and studied their anti-proliferative effects against 3 human cancer cell lines. We show here that pyridine rings can be successful replacements for the trimethoxyphenyl ring, resulting in potent and more soluble analogues. The more straightforward replacement, a 2,6-dimethoxypyridine ring led to inactive analogues, but a 2-methoxy-6-methylsulfanylpyridine moiety led to active analogues when combined with different B rings. This replacement led to potent cytotoxic activity against sensitive human cancer cell lines due to tubulin inhibition, as shown by cell cycle analysis, confocal microscopy, and tubulin polymerization inhibitory activity studies. Cell cycle analysis also showed apoptotic responses following treatment. Docking studies suggested binding at the colchicine site of tubulin and provided a good agreement with the observed SAR. A 2-methoxy-6-methylsulfanylpyridine moiety is a good trimethoxyphenyl ring replacement for the development of new colchicine site ligands.

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