3-Methoxybenzamide

Names

[ Name ]:
3-Methoxybenzamide

[Synonym ]:
3-Methoxybenzamide
MFCD00007986
3-Methoxy-benzoesaeure-amid
3-Methoxy-benzamid
3-methoxy-benzoic acid amide
m-anisamide
Benzamide, 3-methoxy-
Benzamide,3-methoxy
3-Methoxy-benzamide
EINECS 227-379-7
3-Methoxyphenylformamide
m-Methoxybenzamide

Biological Activity

[Description]:

3-Methoxybenzamide (3-MBA), an inhibitor of ADP-ribosyltransferase (ADPRTs) and PARP, inhibits cell division in Bacillus subtilis, leading to filamentation and eventually lysis of cells[1]. 3-Methoxybenzamide (3-MBA) enhances in vitro plant growth, microtuberization, and transformation efficiency of blue potato (Solanum tuberosum L. subsp. andigenum)[2].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Epigenetics >> PARP

Signaling Pathways >> Cell Cycle/DNA Damage >> PARP

[In Vitro]

3-Methoxybenzamide (0-30 mM) affects septation via the FtsZ system during both vegetative growth and sporulation[1]. 3-Methoxybenzamide (3 MB; 0.2 to 0.6 mM) significantly increaseS the growth and microtuber formation of in vitro propagated plants[2]. Cell Viability Assay[1] Cell Line: ftsZ mutant strains. Concentration: 0-30 mM. Incubation Time: 30℃ overnight. Result: Changes directly or indirectly the ability of ftsZ to bind or hydrolyze the guanine nucleotide, ultimately leading to the inhibition of Zring formation.

[References]

[1]. Y Ohashi, et al. The lethal effect of a benzamide derivative, 3-methoxybenzamide, can be suppressed by mutations within a cell division gene, ftsZ, in Bacillus subtilis. J Bacteriol. 1999 Feb;181(4):1348-51.

[2]. Venkateswari J. Chetty, et al. Poly (ADP-ribose) polymerase inhibitor 3-methoxybenzamide enhances in vitro plant growth, microtuberization, and transformation efficiency of blue potato (Solanum tuberosum L. subsp. andigenum). In Vitro Cellular & Developmental Biology - Plant (2020).

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
280.0±23.0 °C at 760 mmHg

[ Melting Point ]:
132.5-135.5 °C(lit.)

[ Molecular Formula ]:
C₈H₉NO₂

[ Molecular Weight ]:
151.163

[ Flash Point ]:
146.8±18.9 °C

[ Exact Mass ]:
151.063324

[ PSA ]:
52.32000

[ LogP ]:
0.85

[ Vapour Pressure ]:
0.0±0.6 mmHg at 25°C

[ Index of Refraction ]:
1.546

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: CV5463333

CHEMICAL NAME :: Benzamide, 3-methoxy-

CAS REGISTRY NUMBER :: 5813-86-5

BEILSTEIN REFERENCE NO. :: 2206857

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C8-H9-N-O2

MOLECULAR WEIGHT :: 151.18

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Mammal - species unspecified

DOSE/DURATION :: 1 gm/kg

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

REFERENCE :: PCJOAU Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) No.1- 1967- Volume(issue)/page/year: 28,335,1994

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
CV5463333

[ HS Code ]:
2924299090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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%

Articles

Characterization of the superinduction of the c-myc proto-oncogene in fibroblasts by benzamide derivatives.

Mol. Cell Biochem. 124(2) , 175-81, (1993)

In mouse fibroblasts stimulated from quiescence into proliferation by serum the induction of expression of the c-myc proto-oncogene is strongly stimulated by 3-methoxybenzamide. Similar superinduction...

Immunosuppressive activities of 6(5H)-phenanthridinone, a new poly(ADP-ribose)polymerase inhibitor.

Int. J. Immunopharmacol. 17(4) , 265-71, (1995)

6(5H)-phenanthridinone, a recently identified poly(ADP-ribose)polymerase (PARP) inhibitor, is able, at micromolar concentrations, to inhibit concanavalin A-induced lymphocyte proliferation and to pote...

Antibacterial alkoxybenzamide inhibitors of the essential bacterial cell division protein FtsZ.

Bioorg. Med. Chem. Lett. 19 , 524-7, (2009)

3-Methoxybenzamide is a weak inhibitor of the essential bacterial cell division protein FtsZ. Exploration of the structure-activity relationships of 3-methoxybenzamide analogues led to the identificat...