2-hydrazinobenzothiazole - CAS 615-21-4
Not Intended for Therapeutic Use. For research use only.
Category:
Inhibitor
Product Name:
2-hydrazinobenzothiazole
Catalog Number:
615-21-4
Synonyms:
2-HYDRAZINOBENZOTHIAZOLE
CAS Number:
615-21-4
Description:
A potent IDO inhibitor
Molecular Weight:
165.22
Molecular Formula:
C7H7N3S
Quantity:
Grams-Kilos
Quality Standard:
In-house
COA:
Inquire
MSDS:
Inquire
Canonical SMILES:
C1=CC=C2C(=C1)N=C(S2)NN
InChI:
1S/C7H7N3S/c8-10-7-9-5-3-1-2-4-6(5)11-7/h1-4H,8H2,(H,9,10)
InChIKey:
JYSUYJCLUODSLN-UHFFFAOYSA-N
Targets:
IDO
Chemical Structure
CAS 615-21-4 2-hydrazinobenzothiazole

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Reference Reading


1.2-Hydrazinobenzothiazole-based etheno-adduct repair protocol (HERP): a method for quantitative determination of direct repair of etheno-bases.
Shivange G1, Kodipelli N1, Anindya R2. DNA Repair (Amst). 2015 Apr;28:8-13. doi: 10.1016/j.dnarep.2015.01.010. Epub 2015 Jan 31.
Etheno-DNA adducts are mutagenic and lead to genomic instability. Enzymes belonging to Fe(II)/2-oxoglutarate-dependent dioxygenase family repair etheno-DNA adducts by directly removing alkyl chain as glyoxal. Presently there is no simple method to assess repair reaction of etheno-adducts. We have developed a rapid and sensitive assay for studying etheno-DNA adduct repair by Fe(II)/2-oxoglutarate-dependent dioxygenases. Using AlkB as model Fe(II)/2-oxoglutarate-dependent dioxygenases, we performed in vitro repair of etheno-adducts containing DNA and detected glyoxal by reacting with 2-hydrazinobenzothiazole which forms complex yellow color compound with distinct absorption spectrum with a peak absorption at 365 nm. We refer this method as 2-hydrazinobenzothiazole-based etheno-adduct repair protocol or HERP. Our novel approach for determining repair of etheno-adducts containing DNA overcomes several drawbacks of currently available radioisotope-based assay.
2.Synthesis of some new benzothiazole derivatives as potential antimicrobial and antiparasitic agents.
Mahran MA1, El-Nassry SM, Allam SR, El-Zawawy LA. Pharmazie. 2003 Aug;58(8):527-30.
Several thiazolidinonyl benzothiazoles 8a-b and thiazolinylbenzothiazoles 9a-j were synthesized by the reaction of 2-(N-substituted thiocarbamoyl hydrazino) benzothiazoles 7a-d with chloroacetic acid or phenacyl bromide respectively. The intermediate compounds 7a-d were prepared in a good yield by the reaction of 2-hydrazinobenzothiazole (6) with phenylisothiocyanates. Synthesis of hydrazones 10a-c were performed by the reaction of 6 with the corresponding aldehydes. Trials to cyclize the obtained hydrazones 10a-c into the corresponding triazolo derivatives 11a-c were unsuccessful. Addition of 4-morphylino carbonyl chloride to compound 6 yielded the corresponding 2-acid hydrazide derivative 12. Some of the prepared compounds were screened for their anti-parasitic activity. Most of them showed reasonable antinematodal or schistosomicidal activity. In addition, antimicrobial screening of all of the prepared new compounds was performed against Staphylococcus aeurus ATCC 6538, Escherichia coli ATCC 8735 and Candida albicans ATCC 10321 but non of them was active.
3.Discovery and characterisation of hydrazines as inhibitors of the immune suppressive enzyme, indoleamine 2,3-dioxygenase 1 (IDO1).
Fung SP1, Wang H, Tomek P, Squire CJ, Flanagan JU, Palmer BD, Bridewell DJ, Tijono SM, Jamie JF, Ching LM. Bioorg Med Chem. 2013 Dec 15;21(24):7595-603. doi: 10.1016/j.bmc.2013.10.037. Epub 2013 Nov 6.
Screening of a fragment library identified 2-hydrazinobenzothiazole as a potent inhibitor of indoleamine 2,3-dioxygenase 1 (IDO1), an enzyme expressed by tumours that suppresses the immune system. Spectroscopic studies indicated that 2-hydrazinobenzothiazole interacted with the IDO1 haem and in silico docking predicted that the interaction was through hydrazine. Subsequent studies of hydrazine derivatives identified phenylhydrazine (IC50=0.25 ± 0.07 μM) to be 32-fold more potent than 2-hydrazinobenzothiazole (IC50=8.0 ± 2.3 μM) in inhibiting rhIDO1 and that it inhibited cellular IDO1 at concentrations that were noncytotoxic to cells. Here, phenylhydrazine is shown to inhibit IDO1 through binding to haem.