6-CHLORO-2,3,4,9-TETRAHYDRO-1H-CARBAZOLE-1-CARBOXAMIDE

ChemicalBook > CAS DataBase List > 6-CHLORO-2,3,4,9-TETRAHYDRO-1H-CARBAZOLE-1-CARBOXAMIDE

6-CHLORO-2,3,4,9-TETRAHYDRO-1H-CARBAZOLE-1-CARBOXAMIDE

Product Name: 6-CHLORO-2,3,4,9-TETRAHYDRO-1H-CARBAZOLE-1-CARBOXAMIDE
CAS No.: 49843-98-3
Chemical Name: 6-CHLORO-2,3,4,9-TETRAHYDRO-1H-CARBAZOLE-1-CARBOXAMIDE
Synonyms: Selisistat;SIRT1 Inhibitor III;EX 527 (SEN0014196);CS-1862;Selisista;SEN0014196;(S)-EX-527;EX 527, >=98%;EX 527; EX527;EX 527 (Selisistat)
CBNumber: CB6230650
Molecular Formula: C13H13ClN2O
Formula Weight: 248.71
MOL File: 49843-98-3.mol

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6-CHLORO-2,3,4,9-TETRAHYDRO-1H-CARBAZOLE-1-CARBOXAMIDE Property

Melting point:: 179.0 to 183.0 °C
Boiling point:: 531.7±38.0 °C(Predicted)
Density: 1.388
storage temp.: 2-8°C
solubility: Soluble in dimethyl sulfoxide, ethanol and dimethyl formamide.
form: powder
pka: 16.12±0.40(Predicted)
color: white to beige
Stability:: Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months

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Safety

Hazard Codes: Xn
Risk Statements: 22-36
Safety Statements: 26
RIDADR: UN 2811 6.1 / PGIII
WGK Germany: 3
HS Code: 2933998090

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

H302Harmful if swallowed

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P337+P313IF eye irritation persists: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: E7034
Product name: EX 527
Purity: ≥98% (HPLC)
Packaging: 5mg
Price: $120
Updated: 2024/03/01

TCI Chemical

Product number: C2739
Product name: 6-Chloro-2,3,4,9-tetrahydro-1H-carbazole-1-carboxamide
Purity: >98.0%(HPLC)
Packaging: 25mg
Price: $280
Updated: 2022/04/27

Alfa Aesar

Product number: J64753
Product name: EX 527
Packaging: 10mg
Price: $126.65
Updated: 2024/03/01

Cayman Chemical

Product number: 10009798
Product name: EX 527
Purity: ≥98%
Packaging: 5mg
Price: $32
Updated: 2024/03/01

Sigma-Aldrich

Product number: E7034
Product name: EX 527
Purity: ≥98% (HPLC)
Packaging: 25mg
Price: $293.4
Updated: 2024/03/01

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6-CHLORO-2,3,4,9-TETRAHYDRO-1H-CARBAZOLE-1-CARBOXAMIDE Chemical Properties,Usage,Production

Description

EX-527 (49843-98-3) is a selective SIRT1 inhibitor (IC50=98 nM). Does not inhibit other HDACs or SIRT family members. Increases p53 acetylation following DNA damage. Cell permeable.

Uses

EX-527 has been used:

in 1% dimethyl sulfoxide, 30%, polyethylene glycol-400 and 1% Tween 80 for treating C57BL/6 N mice to study its effect on intestinal morphological changes and crypt cell apoptosis
as a an inhibitor of sirtuin 1, in treating human cancer lines MCF-7 (Michigan cancer foundation-7) and HCT116 (colon cancer cell line) incubated in Dulbecco′s modified Eagle′s medium, to study its effect on mitochondrial ATP (adenosine triphosphate) production
Intracerebroventricularly infused in rat model of epileptogenesis, to access kainic acid–induced status epilepticus stimulated sirtuin 1 activity

Uses

A selective inhibitor of SIRT1 over SIRT2 and SIRT3

Uses

EX-527 is a potent and selective sirtuin 1 (SIRT1) inhibitor (IC50 38 nM) identified from a high throughput screen. EX-527 is more selective (200-500-fold) for SIRT1 than for SIRT2 or SIRT3 and has been shown to be a potent SIRT6 inhibitor using H3K56 deacetylation site based substrate. EX-527 does not inhibit class I/II HDAC activity at concentrations up to 100uM. Enhances p53 acetylation in response to DNA damaging agents. EX-527 is racemic; the active isomer (EX-243) gives similar results and potency whereas the other isomer (designated EX-242) is inactive.

Definition

ChEBI: 6-chloro-2,3,4,9-tetrahydro-1H-carbazole-1-carboxamide is a member of the class of carbazoles that is 2,3,4,9-tetrahydro-1H-carbazole which is substituted at position 1 by an aminocarbohyl group and at position 6 by a chlorine. It is a member of carbazoles, a monocarboxylic acid amide and an organochlorine compound.

General Description

A cell-permeable indole compound that acts as a potent and highly selective inhibitor of SIRT1 (IC₅₀ = 98 nM). It inhibits other sirtuin family deacetylases only at much higher concentrations (IC₅₀ = 19.6 and 48.7 μM for SIRT2 and SIRT3, respectively) and shows no inhibitory effect against class I and II HDACs or NAD glycohydrolase even at concentrations as high as 100 μM. Shown to be orally bioavailable with a serum half-life of 136 minutes in mice in vivo.

Biological Activity

Selective inhibitor of SIRT1 that does not inhibit histone deacetylase (HDAC) or other sirtuin deacetylase family members (IC 50 values are 98, 19600, 48700, > 100000 and > 100000 nM for SIRT1, SIRT2, SIRT3, HDAC and NADase respectively). Enhances p53 acetylation in response to DNA damaging agents.

Biochem/physiol Actions

Primary TargetSIRT1

storage

Store at +4°C

References

1) Napper et al. (2005), Discovery of indoles as potent and selective inhibitors of the deacetylase SIRT1; J. Med. Chem., 48 8045 2) Solomon et al. (2006) Inhibition of SIRT1 catalytic activity increases p53 acetylation but does not alter cell survival following DNA damage; Mol. Cell, 26 28 3) Gertz et al. (2013) EX-527 inhibits Sirtuins by exploiting their unique NAD+-dependent deacetylation mechanism; Proc. Natl. Acad. Sci. USA, 110 e2772

6-CHLORO-2,3,4,9-TETRAHYDRO-1H-CARBAZOLE-1-CARBOXAMIDE Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 6-CHLORO-2,3,4,9-TETRAHYDRO-1H-CARBAZOLE-1-CARBOXAMIDE manufacturers

Henan Aochuang Chemical Co.,Ltd.

Product: 6-CHLORO-2,3,4,9-TETRAHYDRO-1H-CARBAZOLE-1-CARBOXAMIDE 49843-98-3
Price: US $0.00-0.00/KG
Min. Order: 1KG
Purity: 98%
Supply Ability: 1Ton
Release date: 2022-10-13

Career Henan Chemical Co

Product: 6-CHLORO-2,3,4,9-TETRAHYDRO-1H-CARBAZOLE-1-CARBOXAMIDE 49843-98-3
Price: US $8.80/KG
Min. Order: 1KG
Purity: 97%-99%
Supply Ability: 100kg
Release date: 2019-07-12

49843-98-3, 6-CHLORO-2,3,4,9-TETRAHYDRO-1H-CARBAZOLE-1-CARBOXAMIDERelated Search:

6-Chloro-4-phenylquinazolin-2-carboxaldehyde Everolimus SIRTINOL MK-2206 2HCl Trametinib SRT1720 PLX4032 6-CHLORO-1,2,3,4-TETRAHYDRO-ISOQUINOLINE HYDROCHLORIDE 6-CHLORO-1,2,3,4-TETRAHYDROQUINOLINE 6-Chloro-1,2,3,4-tetrahydroisoquinoline 6-chloro-5-methoxy-2,3-dihydro-1H-inden-1-one 6-Chloro-1,3-dimethyl-2,4-(1H,3H)-pyrimidinedione 2(1H)-Pyrimidinone, 4-chloro- (6CI,9CI) 6-CHLORO-2,3,4,9-TETRAHYDRO-1H-CARBAZOLE-1-CARBOXYLIC ACID 6-CHLORO-4-METHYL-1-INDANONE 6-CHLORO-5-METHYLPYRIDINE-3-CARBALDEHYDE 6-chloro-7-fluoro-2,3-dihydro-1H-inden-1-one 6-Chloro-7-Bromoindanone

6-CHLORO-2,3,4,9-TETRAHYDRO-1H-CARBAZOLE-1-CARBOXAMIDE

6-CHLORO-2,3,4,9-TETRAHYDRO-1H-CARBAZOLE-1-CARBOXAMIDE, >95%

Selisistat

EX 527 (SEN0014196)

(S)-6-chloro-2,3,4,9-tetrahydro-1H-carbazole-1-carboxamide

SEN0014196

6-Chloro-2,3,4,9-tetrahydro-1H-carbazole-1-carboxamide EX-527 Selisistat

EX 527, >=98%

EX 527 (Selisistat)

Selisistat 6-Chloro-2,3,4,9-tetrahydro-1H-carbazole-1-carboxaMide

SIRT1 Inhibitor III

Selisistat - EX 527

EX 527; EX527

CS-1862

SELISISTAT;EX 527;EX527;SEN0014196

EX-527; EX-527; EX-527; SELISISTAT.

6-Chloro-2,3,4,9-tetrahydro-1H-carbazole-1-carboxamide &gt

(S)-EX-527

1H-Carbazole-1-carboxamide, 6-chloro-2,3,4,9-tetrahydro-

6-CHLORO-2,3,4,9-TETRAHYDRO-1H-CARBAZOLE-1-CARBOXAMIDE USP/EP/BP

Selisistat (SEN0014196

SIRT1 Inhibitor III EX-527 EX527

EX-527/SEN0014196, EX527

Selisista

49843-98-3

C13H13ON2Cl

Inhibitors

Inhibitor

Other enzyme inhibitors and activators