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

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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
  • Pifithrin-α (PFTα) hydrobromide
  • EX-527, SIRT1 Inhibitor
  • 6-Chloro-2,3,4,9-tetrahydro-1H-Carbazole-1-carboxamide/Selisistat
  • 49843-98-3
  • C13H13ON2Cl
  • Inhibitors
  • Inhibitor
  • Other enzyme inhibitors and activators