2-Chloro-N-(3,4-dimethoxybenzyl)acetamide

Names

[ Name ]:
2-Chloro-N-(3,4-dimethoxybenzyl)acetamide

[Synonym ]:
Chlor-essigsaeure-veratrylamid
N-chloroacetyl-3,4-dimethoxybenzylamine
C-Chlor-N-veratryl-acetamid
2-chloro-N-(3,4-dimethoxybenzyl)acetamide
chloro-acetic acid veratrylamide
N-(3.4-Dimethoxy-benzyl)-chloracetamid
2-Chloro-N-((3,4-dimethoxyphenyl)methyl)acetamide
N-(Dimethoxy-3,4 benzyl)-chloroacetamide [French]
Acetamide,2-chloro-N-((3,4-dimethoxyphenyl)methyl)
N-Chloracetyl-(3,4-dimethoxyphenyl)methylamin
DKM 2-93

Biological Activity

[Description]:

DKM 2-93 is a relatively selective inhibitor of UBA5 with an IC50 of 430 μM.

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> E1/E2/E3 Enzyme

Research Areas >> Cancer

[Target]

IC50: 430 μM (UBA5), 90 μM (PaCa2 cells), 30 μM (Panc1 cells)[1]

[In Vitro]

Ubiquitin-like modifier activating enzyme 5 (UBA5) is a novel pancreatic cancer therapeutic target. DKM 2-93 impairs pancreatic cancer cell survival through covalently modifying the catalytic cysteine of UBA5, thereby inhibiting its activity as a protein that activates the ubiquitin-like protein UFM1 to UFMylate proteins. DKM 2-93 inhibits PaCa2 and Panc1 cells survival with IC50s of 90 and 30 μM, respectively[1].

[In Vivo]

DKM 2-93 daily treatment significantly impairs tumor growth of PaCa2 cells in vivo in tumor xenograft studies in immune-deficient mice without causing any weight loss or overt toxicity[1].

[Cell Assay]

PaCa2 and Panc1 cells are treated with 0-1000 μM DKM 2-93 for 48 hours. Cell viability is assessed by Hoescht stain[1].

[Animal admin]

Mice: Mice are subcutaneously injected with PaCa2 cells to initiate the tumor xenograft study and treatments of mice are initiated with vehicle or DKM 2-93 (50 mg/kg ip, once per day) three days after injection of cancer cells[1].

[References]

[1]. Roberts AM, et al. Chemoproteomic Screening of Covalent Ligands Reveals UBA5 As a Novel Pancreatic Cancer Target. ACS Chem Biol. 2017 Apr 21;12(4):899-904.

[Related Small Molecules]

Ginkgolic acid C15:1 | PYR-41 | NSC232003 | CC122 | SZL P1-41 | TAK-243(MLN7243) | PRT 4165 | SKPin C1 | TZ9 | CC 0651 | 2-D08 | PYZD 4409 | CC-885 | COH000

Chemical & Physical Properties

[ Density]:
1.194g/cm3

[ Boiling Point ]:
425.7ºC at 760 mmHg

[ Molecular Formula ]:
C₁₁H₁₄ClNO₃

[ Molecular Weight ]:
243.68700

[ Flash Point ]:
211.3ºC

[ Exact Mass ]:
243.06600

[ PSA ]:
47.56000

[ LogP ]:
1.94970

[ Index of Refraction ]:
1.522

[ Storage condition ]:
2-8℃

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AB5429210

CHEMICAL NAME :: Acetamide, 2-chloro-N-((3,4-dimethoxyphenyl)methyl)-

CAS REGISTRY NUMBER :: 65836-72-8

BEILSTEIN REFERENCE NO. :: 2857211

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C11-H14-Cl-N-O3

MOLECULAR WEIGHT :: 243.71

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >400 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: APFRAD Annales Pharmaceutiques Francaises. (SPPIF, B.P.22, F-41353 Vineuil, France) V.1- 1943- Volume(issue)/page/year: 41,457,1983

Safety Information

[ Hazard Codes ]:
Xi

[ HS Code ]:
2924299090

Synthetic Route

Click to get detail synthetic route

Customs

[ HS Code ]: 2924299090

[ Summary ]:
2924299090. other cyclic amides (including cyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%