615-21-4

Usage

Uses

Used in Spectrophotometric Analysis:
2-Hydrazinobenzothiazole is used as a reagent in the spectrophotometric analysis for the determination of methenamine and its salts. It aids in the accurate measurement and quantification of these compounds by forming a colored complex that can be detected and measured using spectrophotometry.
Used in Etheno-DNA Adduct Detection and Repair Mechanism:
In the field of molecular biology and genetics, 2-Hydrazinobenzothiazole plays a crucial role in the detection and repair mechanism of etheno-DNA adducts. Etheno-DNA adducts are DNA lesions formed by the covalent binding of an etheno bridge between two adjacent nucleotides, which can lead to mutations and genomic instability. 2-Hydrazinobenzothiazole is employed as a tool to identify these adducts and facilitate their repair, thus contributing to the maintenance of genetic integrity and prevention of diseases associated with DNA damage.

InChI:InChI=1/C7H7N3S/c8-10-7-9-5-3-1-2-4-6(5)11-7/h1-4H,8H2,(H,9,10)

Upstream product

• 136-95-8 2-amino-benzthiazole 
• 615-20-3 2-chlorobenzo[d][1,3]thiazole 
• 934-34-9 2(3H)-Benzothiazolone 
• 149-30-4 2-thioxo-3H-1,3-benzothiazole 
• 120-78-5 di(benzothiazol-2-yl)disulfide 
• 149-30-4 2-Mercaptobenzothiazole 
• 7803-57-8 hydrazine hydrate 
• 62-53-3 aniline 
• 2644-70-4 hydrazine hydrochloride 
• 95-16-9 1,3-Benzothiazole 
• 103-85-5 monophenylthiourea 

Downstream Products

• 3790-06-5 (E)-2-(2-(benzo[d][1,3]dioxol-5-ylmethylene)hydrazinyl)benzo[d]thiazole 
• 99845-70-2 TM-N1091 
• 18672-63-4 1-Acetyl-2-benzothiazolylhydrazine 
• 72758-11-3 2-benzo[4,5]thiazolo[2,3-c][1,2,4]triazol-3-yl-phenol 
• 41814-44-2 1,2,4-triazolo<4,3-b>benzothiazol-3(2H)-one 
• 3837-57-8 acetaldehyde (2-benzothiazolyl)hydrazone 
• 114723-36-3 4-methoxy-benzoic acid-(N'-benzothiazol-2-ylhydrazide) 
• 247-92-7 s-triazolo<3,4-b>benzothiazol 
• 41814-60-2 3-methyl[1,2,4]triazolo[3,4-b][1,3]benzothiazole 
• 248-02-2 [1,2,3,4]tetrazole[5,1-b][1,3]benzothiazole 
• 22295-51-8 3--2-chlor-1,4-naphthochinon 
• 51287-67-3 Pyridin-4-carbaldehyd-benzothiazol-2-ylhydrazon 
• 63190-61-4 pyridine-3-carbaldehyde benzothiazol-2-yl-hydrazone 
• 136740-27-7 3-(Benzothiazol-2-ylamino)-5-[1-(4-hydroxy-3-methoxy-phenyl)-meth-(Z)-ylidene]-2-phenyl-3,5-dihydro-imidazol-4-one 

Relevant academic research and scientific papers

Six-membered spirocycle triggered probe for visualizing Hg2+ in living cells and bacteria-EPS-mineral aggregates

A novel rhodamine based probe with a unique six-membered spirocycle was rationally designed for detection of Hg2+ with greatly improved selectivity, sensitivity, and photostability. The probe has been shown to be suitable for Hg2+ imaging in living cells and mapping Hg2+ distribution in living cell-EPS-mineral aggregates under anoxic conditions.

An AIE and PET fluorescent probe for effective Zn(ii) detection and imaging in living cells

A sensitive fluorescent probe L for Zn2+ with aggregation-induced emission (AIE) properties has been synthesized. The probe L exhibits specific selectivity and high sensitivity towards Zn2+ in EtOH/H2O (4?:?1, v/v, HEPES = 20 mM, pH = 7.20) solvents, with the detection limit of 2.1 × 10-8 M. The potential sensing mechanism was analyzed via Job plot, MS and NMR titration, and the complexation ratio of the probe L and Zn2+ was 1?:?1. Furthermore, the as-prepared probe shows high sensitivity towards Zn2+ in a pH range of 4.8-12.0, combined with its wonderful cell permeability which ensures that it can work under physiological conditions and can image Zn2+ in living cells.

Selective “off-on” detection of magnesium (II) ions using a naphthalimide-derived fluorescent probe

A novel “off-on” fluorescent probe based on 1, 8-naphthalimide derivative for the detection of Mg2+ in ethanol solution was designed and synthesized. The probe displayed responses to Mg2+ with a fluorescence enhancement at 523 nm, accompanying with a distinct fluorescence change from nearly colorless to bright yellow-green. Besides, the probe showed a rapid detection process (45 s), high fluorescence enhancement (up to 15-fold), a good binding constant (6.17 × 105 M?1) and a low detection limit of Mg2+ (5.01 × 10?8 M). Moreover, density functional theory (DFT) calculations were also performed to support the responding mechanism between the probe and the coordination complex. In addition, the cell cytotoxicity experiments suggested that the probe is nearly non-toxic and the fluorescence scanning microscopic experiments demonstrated that the probe was capable of monitoring at the intracellular Mg2+ level successfully.

Crystallographic investigations of benzothiazol-2-yl-hydrazine

The title compound crystallizes in the monoclinic space group P2 1/n with unit cell parameters a = 10.842(9), b = 5.750(7), c = 12.964(6) A, β = 110.13(6)°, V = 758.8(11) A3 and Z = 4. The final reliability index is 0.060 for 1034 observed reflections. The five-membered heterocyclic thiazole ring is coplanar with its fused benzene ring. The crystal structure is stabilized by two intermolecular N-H...N hydrogen bonded interactions.

In situ oxidation triggered heteroleptically deprotonated cobalt(III) and homoleptic nickel(II) complexes of diacetyl monoxime derived tri-nitrogen chelators; Synthesis, molecular structures and biological assay

Two tri-nitrogen chelating unsymmetrical Schiff base ligands, 3-(hydroxyimino)-2-butanone-2-(1H-benzothiazol-2-yl)hydrazone and 3-(hydroxyimino)-2-butanone-2-(1H-benzimidazol-2-yl)hydrazone are synthesized by the condensation reaction of diacetyl monoxime with 2-hydrazino-benzothiazole/benzimidazole. Ligands have shown ML2 type octahedral coordination towards Ni(II) and in situ generated Co(III) ions. Ligands and complexes are characterized by various spectro-analytical techniques. Both the ligands have shown a similar mode of ligation, but a different mode of deprotonation towards the cobalt and nickel ions. Ligands are left neutral in the case of nickel complexes while anionic in the case of cobalt complexes. Further, in situ oxidation of Co(II) to Co(III) has triggered a different mode of deprotonation between the two ligands of the same cobalt complex. Out of the four complexes synthesized, three complexes are characterized by single crystal X-ray diffraction technique, to evidence the structural facts. A comparative account of bond lengths of two complexes of the benzothiazole based ligand is presented. Structures of all the four complexes have been checked preliminarily for their NCI-60 Human Cancer Cell Line anticancer screening. Further, one among the four, the nickel complex of benzothiazole core is used for one dose growth inhibition screening against 60 different human cancer cell lines. The tested complex has shown highest growth inhibition over a Non-Small Cell Lung Cancer cell line EKVX. In addition, compounds are screened for their antibacterial and antifungal potencies against few microorganisms. The complexes have shown promising antimicrobial potencies.

[Dichlorido (2-(2-(1H-benzo[d]thiazol-2-yl)hydrazono)propan-1-ol) Cu(II)]: Crystal structure, Hirshfeld surface analysis and correlation of its ESI-MS behavior with [Dichlorido 3-(hydroxyimino)-2-butanone-2-(1H-benzo[d]thiazol-2-yl)hydrazone Cu(II)]

In the present work, Cu(II) complexes of 2-(2-benzo[d]thiazol-2-yl)hydrazono)propan-1-ol (L1) and 3-(hydroxyimino)-2-butanone-2-(1H-benzo[d]thiazol-2-yl)hydrazone (L2) are synthesized and characterized by various spectro-analytical techniques. The structure of Cu(II) complex of L1 i.e., [CuL1Cl2], is unambiguously determined by single crystal X-ray diffraction method. While similar efforts were unsuccessful in the case of Cu(II) complex of L2 i.e., [CuL2Cl2]. Hence, to avail the structural facts, various cationic/anionic fragments or adducts formed during positive/negative mode electrospray ionization (ESI) of CuL1Cl2 and CuL2Cl2 have been identified with the help of their charge, monoisotopic masses and isotopic distributions. The similarity in the ESI behavior of two complexes has inferred their structural resemblance, which is further supported by DFT optimized structures, EPR spectral studies and analytical measurements. The EPR spectral behavior (g|| > g⊥ > 2.02) of the complexes are attributed to an axial symmetry with the dx2?y2 ground state having square pyramidal Cu(II) ion. CuL1Cl2 has crystallized in monoclinic crystal system in P21/c space group. The molecular complex has ring-metal (Cg-Me) interactions of the type Cg···>Cu, which contributes to the crystal packing. The Cl?H (30.6%) interactions have the major contribution among all intermolecular contacts and have played a vital role in the stabilization of the molecular structure, which is extended to 3D network through C–H···Cg and Cg-Cg interactions.

Functionalized 2-hydrazinobenzothiazole with isatin and some carbohydrates under conventional and ultrasound methods and their biological activities

Several chemical reactions were carried out on 3-(benzothiazol-2-yl-hydrazono)-1,3-dihydro-indol-2-one (2). 3-(Benzothiazol-2-yl-hydrazono)-1-alkyl-1,3-dihydro-indol-2-one 3a-c have been achieved. Reaction of compound 2 with ethyl bromoacetate in the presence of K2CO3 resulted the uncyclized product 4. Reaction of compound 2 with benzoyl chloride afforded dibenzoyl derivative 5. Compound 2 was smoothly acetylated by acetic anhydride in pyridine to give diacetyl derivative 6b. Moreover, when compound 4 reacted with methyl hydrazine, it yielded dihydrazide derivative 7, whereas the hydrazinolysis of this compound with hydrazine hydrate gave the monohydrazide derivative 8. {N-(Benzothiazol-2-yl-N'-(3-oxo-3,4-dihydro-2H- 1,2,4-triaza-fluoren-9-ylidene)hydrazino]-acetic acid ethyl ester (9) was prepared by ring closure of compound 8 by the action of glacial acetic acid. In addition, the reaction of 2-hydrazinobenzothiazole (1) with D-glucose and D-arabinose in the presence of acetic acid yielded the hydrazones 10a,b, respectively. Acetylation of compound 10b gave compound 11b. On the other hand, compound 13 was obtained by the reaction of compound 1 with gama-D-galactolactone (12). Acetylation of compound 13 with acetic anhydride in pyridin gave the corresponding N1-acetyl-N2-(benzothiazolyl)-2-yl)-2,3,4,5,6-penta-O-acetyl-D-galactohydrazide (14). Better yields and shorter reaction times were achieved using ultrasound irradiation. The structural investigation of the new compounds is based on chemical and spectroscopic evidence. Some selected derivatives were studied for their antimicrobial and antiviral activities.

Synthesis, structural investigations, DFT, molecular docking and antifungal studies of transition metal complexes with benzothiazole based Schiff base ligands

A novel series of complexes of the type, [ML2].nH2O, [where L = 2-(α-methyl salicylidene–2′-imino) aminobenzo thiazole (HMAB), 2-(α-phenyl salicylidene–2′-imino) aminobenzo thiazole (HPAB), 2-(o-Vanillidene–2′-imino) amino benzothiazole (HVAB)] have been reported. These Schiff bases and their transition metal complexes were fully characterized by several physico-chemical and spectral techniques, which revealed the tridentate chelation of ligand. The DFT calculations of these reported compounds were made to obtain bonding inside the structure by GAUSSIAN 03 programme platforms. The QSAR study was performed by HyperChem Professional 8.0.3 software to explain the biological effeteness of the ligands. A docking analysis using the AutoDock Vina software was carried out to understand the binding pattern of the investigated compounds towards target proteins CYP121 and CYP51 from Mycobacterium tuberculosis. Furthermore, all the compounds have been reported to exhibit significant antifungal activity when tested against Aspergillus flavus and Aspergillus niger.

Novel benzo[4,5]thiazolo[2,3-C][1,2,4]triazoles: Design, synthesis, anticancer evaluation, kinase profiling and molecular docking study

In the current study, we report the synthesis and cytotoxic evaluation of a new series of S-benzo[4,5]thiazolo[2,3-c][1,2,4]triazole-based derivatives 8-12. Cytotoxicity of the new compounds was investigated in A549, MCF-7, and Hep3B cancer cell lines. Among these derivatives, compound 12 bearing an isatin moiety was the most active derivative (IC50 = 2.40-3.53 μM). A mechanistic study of compound 12 was performed using the kinase profiling test to explore its inhibitory activity against 10 types of the oncogenic kinases and the potential activation of caspase 3/7 enzymes. The results revealed that compound 12 showed moderate inhibition of the EGFR and LCK kinases. Moreover, compound 12 also activated caspase-3/7 in A549 cells. The docking study of compound 12 into EGFR ATP-active site revealed that it fits nicely with good binding affinity. Together, the results indicated that compound 12 could serve as a good lead for developing new potential anticancer agents.

Synthesis, biological evaluation and kinase profiling of novel S-benzo[4,5]thiazolo[2,3-c][1,2,4]triazole derivatives as cytotoxic agents with apoptosis-inducing activity

A novel set of S-benzo[4,5]thiazolo[2,3-c][1,2,4]triazoles was synthesized. Cytotoxicity of these compounds was evaluated against three cancer cell lines of different origins, Hep3B, A549, and MCF-7. Three of these compounds were screened by NCI for growth inhibitory activities against 60 cancer cell lines. The results revealed significant cytotoxic activities for compounds 13a-i. Among these derivatives, compounds 13c and 13f-13i exhibited the highest cytotoxicity against the selected cancer cell lines with IC50 values between 3.17 and 14.18 μM. The structure-activity relationship of compounds 13a-i indicated favorable cytotoxic results on the expansion of the cyclic amine and the substitution with aminothiazole moiety. A mechanistic study revealed the activation of caspase-3/7 in A549 cells on treatment with compounds 13f-i at 5–20 μM. Moreover, the results of flow cytometric analysis suggested that compound 13i efficiently induced apoptosis in a dose-dependent manner. Compounds 13f,g,i also exhibited a weak to moderate inhibition of multiple kinases where compound 13i was the most active in inhibiting the activity of CDK2/Cyclin A1 (IC50 = 4.65 μM). The current work provided a novel set of compounds with cytotoxic, kinase inhibition, and apoptosis-inducing activities, which can serve as a lead for further optimization.