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KGN

KGN structure

CAS No:
4727-31-5
Formula:
C20H15NO3
Chemical Name:
KGN
Synonyms:
2-[([1,1'-Biphenyl]-4-ylaMino)carbonyl]benzoic Acid;2-[(Biphenyl-4-yl)carbaMoyl]benzoic Acid;4'-Phenylphthalanilic Acid;Kartogenin;KGN;2-([1,1'-biphenyl]-4-ylcarbaMoyl)benzoic acid;4′-Phenyl-phthalanilic acid (8CI);Kartogenin(KGN)
Categories:
Biochemical Engineering > Inhibitors

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Description

Kartogenin is an inducer of differentiation of human mesenchymal stem cells into chondrocytes.

KGN Basic Attributes

Molecular Weight：

317.338

Exact Mass：

317.105194

UNII：

Q93BBN11CP

DSSTox ID：

DTXSID30385074

HScode：

2924299090

Characteristics

PSA：

66.4

XLogP3：

4.2

Density：

1.3±0.1 g/cm3

Melting Point：

272 °C

Flash Point：

234.6±26.8 °C

Refractive Index：

1.674

Water Solubility：

DMSO: >15mg/mL

Storage Conditions：

room temp

Safety Information

Transport codes：

UN 3077 9 / PGIII

wgk germany：

hazard class code：

22-36-50/53

safety instructions：

60-61

Marks：

Xn,N

Precautionary statement(s)：

P273-P305 + P351 + P338-P501

Hazard Statements：

H302-H319-H410

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P273, P280, P301+P312, P305+P351+P338, P330, P337+P313, P391, and P501|Aggregated GHS information provided by 39 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH Entry Terms：

2-(4-biphenylylcarbamoyl)benzoic acid

KGN Use and Manufacturing

Methods of Manufacturing

Before the PEGylation was carried out on a General procedure: DCC (0.9equiv) and DMAP (0.2 equiv) were added to a solution of the selected alcohol (1.2 equiv) in CH2C12/DMSO (2:1; 0.1 M) at 0 C. The mixture was stirred for 30 mm before acid (1 equiv) was introduced and stirring continued for 12 h at ambient temperature. For work up, all volatile materials were evaporated, the product adsorbed on silica and purified by flash chromatography (hexanes/ethyl acetate) to give the desired product (yield .-75%).General procedure: To a solution of acid and diisopropylethylamine (DIEA, 2.2 equiv) in DMF (0.1 M concentration) at 00 C. was added the corresponding amine 1.2 equiv). The mixture was stirred for 30 mm and PyBOP (1.1 equiv) was added and stirred at room temperature for 6 h. The slurry reactionmixture was washed with brine (x5 to assure complete removal of DMSO; volume of brine .-10 times volume of DMSO). The aqueous solution was then extracted with ethyl acetate (x3) and dried over sodium sulfate. Combined organic phases were concentrated under reduced pressureand adsorbed on silica gel to be purified by flash chromatography to afford the desired amide.benzylidene derivatives: for example ... 3-(2, 4, 6-TRIMETHYLBENZOYL)-2-BIPHENYLCARBOXYLIC ACID, 2'-BENZYLCARBAMOYLBIPHENYL-2-CARBOXYLIC ACID, 3-CHLORO-3'-METHYLBIPHENYL-2, 2'-DICARBOXYLIC ACID, 2-HO-5-(4'-HO-BIPHENYL-4-YLAZO)BENZOIC ACID, General procedure: To a solution of phthalic anhydride (1.05 equiv) in a 3:1mixture of chioroformlTHF (0.05 M concentration) wasadded the corresponding amine (RArNH2, 1 equiv). Themixture was stirred overnight at room temperature. Thereaction mixture was washed with brine (x2). The aqueoussolution was then extracted with ethyl acetate (x3) and driedover sodium sulfate. Combined organic phases were concentrated under reduced pressure and adsorbed on silica gelto be purified by flash chromatography to afford the desiredamide.

Uses

Kartogenin is a potent, selective, and non-cytotoxic downstream RUNX1 and RUNX2 modulator. Kartogenin causes mesenchymal stem cells found in joints to differentiate into chondrocyte cells that can build cartilage where it has been destroyed.

Computed Properties

Molecular Weight:317.3
XLogP3:4.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:317.10519334
Monoisotopic Mass:317.10519334
Topological Polar Surface Area:66.4
Heavy Atom Count:24
Complexity:436
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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4727-31-5 2-[(4-phenylphenyl)carbamoyl]benzoic acid

CAS No.: 4727-31-5

Grade: Industrial Grade

Content: 95%

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