4-(4-methylpiperazin-1-yl)-7-nitro-3-oxido-2,1,3-benzoxadiazol-3-ium

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H13N5O4
Molecular Weight	279.252
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of 4-(4-methylpiperazin-1-yl)-7-nitro-3-oxido-2,1,3-benzoxadiazol-3-ium

Structure Search

SMILES

CN1CCN(CC1)C2=CC=C(C3=NO[N+]([O-])=C23)[N+]([O-])=O

InChI

InChIKey=MWFZDJLPWDCQIL-UHFFFAOYSA-N

InChI=1S/C11H13N5O4/c1-13-4-6-14(7-5-13)9-3-2-8(15(17)18)10-11(9)16(19)20-12-10/h2-3H,4-7H2,1H3

HIDE SMILES / InChI

Molecular Formula	C11H13N5O4
Molecular Weight	279.252
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21075910
Curator's Comment: description was created based on several sources, including http://google.com/patents/WO2011014825A3 | https://www.google.com/patents/WO2015054374A3 | https://www.ncbi.nlm.nih.gov/pubmed/26095524 | https://www.ncbi.nlm.nih.gov/pubmed/26311300

NSC-207895 (XI-006) is a derivative of nitrobenzofuroxan and an anticancer agent with an EC50 of 1 μM. NSC-207895 also upregulated the expression of p53 in MCF-7 cells that led to increased expression of proapoptotic genes including PUMA, BAX, as well as PIG3. Notably, NSC-207895, also called a small-molecule p53 activator, gives rise to MCF-7 cells to experience apoptosis and decrease the viability of cancer cells along with nutlin-3a, which dissociated the MDM2-p53 complex. NSC-207895 is an electrophilic compound that has antitumor and mutagenic activities. NSC-207895 may lead to the damage of DNA that inhibits the growth of tumors.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cellular tumor antigen p53 21 Target ID: CHEMBL4096 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21075910	Activator 1447

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 609 Sources: http://google.com/patents/WO2011014825A3	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Accelerating the discovery of biologically active small molecules using a high-throughput yeast halo assay.	2007-03	17291044

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

MCF-7 cells were treated with 0.5 mg/mL of DOX or XI-006 (NSC-207895, 1, 2, 5 mkM) for 16 hours and lysed to measure p53 phosphorylation levels.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:01:16 GMT 2025` Edited by `admin` on `Mon Mar 31 19:01:16 GMT 2025`
Record UNII	63J576F4C5
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-179940

Preferred Name

English

4-(4-methylpiperazin-1-yl)-7-nitro-3-oxido-2,1,3-benzoxadiazol-3-ium

Systematic Name

English

7-(4-methylpiperazin-1-yl)-4-nitrobenzo[c][1,2,5]oxadiazole 1-oxide

Systematic Name

English

4-(4-Methyl-1-piperazinyl)-7-nitro-2,1,3-benzoxadiazole 3-oxide

Systematic Name

English

METHYL-1-PIPERAZINYL)-7-NITRO-BENZOFURAZAN 3-OXIDE, 4-(4-

Common Name

English

XI-006

Code

English

2,1,3-Benzoxadiazole, 4-(4-methyl-1-piperazinyl)-7-nitro-, 3-oxide

Systematic Name

English

NSC-207895

Code

English

Benzofurazan, 4-(4-methyl-1-piperazinyl)-7-nitro-, 3-oxide

Systematic Name

English

Code System Code Type Description

NSC

207895