Production Method 1

7716-66-7

87691-87-0

Reaction Conditions

1.1 Solvents: Ethanol ;  36 h, 80 °C

Reference

An efficient synthesis and biological screening of benzofuran and benzo[d]isothiazole derivatives for Mycobacterium tuberculosis DNA GyrB inhibition

Reddy, Kummetha Indrasena; et al, Bioorganic & Medicinal Chemistry, 2014, 22(23), 6552-6563

Production Method 2

2634-33-5

87691-87-0

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride Solvents: Dichloromethane
1.2 -

Reference

Synthesis and biological evaluation of novel isoxazolines linked via piperazine to 2-benzoisothiazoles as potent apoptotic agents

Byrappa, Sathish; et al, European Journal of Medicinal Chemistry, 2017, 126, 218-224

Production Method 3

23031-78-9

87691-87-0

Reaction Conditions

1.1 Reagents: Sodium nitrite
1.2 Reagents: Cupric chloride
2.1 Solvents: Toluene ;  110 °C

Reference

Preparation of 3-(1-piperazinyl)-1,2-benzisothiazole hydrochloride (1:1) (ZPR intermediate)

Anonymous, IP.com Journal, 2008, 8,

Production Method 4

7716-66-7

87691-87-0

Reaction Conditions

1.1 Solvents: tert-Butanol ;  15 h, 120 °C; 120 °C → 30 °C
1.2 Reagents: Sodium hydroxide Solvents: Water ;  pH 12 - 14, 20 - 30 °C

Reference

Synthesis of Novel 3-(Piperazin-1-yl)-1,2-benzothiazole Derivatives and Their Antibacterial Activity

Garlapati, Krishna Kanth; et al, Russian Journal of Organic Chemistry, 2022, 58(10), 1534-1541

Production Method 5

87691-87-0

Reaction Conditions

1.1 Reagents: Thionyl chloride Solvents: Chlorobenzene
1.2 Reagents: Chlorine
1.3 -

Reference

Preparation of benzisothiazole derivatives

, World Intellectual Property Organization, , ,

Production Method 6

119-80-2

87691-87-0

Reaction Conditions

1.1 Reagents: Thionyl chloride
2.1 Reagents: Ammonium hydroxide ,  Chlorine
3.1 Reagents: Phosphorus oxychloride
4.1 -

Reference

1,2-Benzisothiazol-3-ylpiperazines

, Federal Republic of Germany, , ,

Production Method 7

119-80-2

87691-87-0

Reaction Conditions

1.1 Reagents: Thionyl chloride Solvents: Dimethylformamide ,  Toluene
2.1 Reagents: Ammonium hydroxide ,  Chlorine Solvents: Dichloromethane
3.1 Reagents: Phosphorus oxychloride
4.1 -

Reference

Synthesis and biological evaluation of 1-(1,2-benzisothiazol-3-yl)- and (1,2-benzisoxazol-3-yl)piperazine derivatives as potential antipsychotic agents

Yevich, Joseph P.; et al, Journal of Medicinal Chemistry, 1986, 29(3), 359-69

3-piperazin-1-yl-1,2-benzothiazole Raw materials

• 1,2-Benzothiazol-3-amine
• 3-chloro-1,2-benzothiazole
• Benzoisothiazol-3-one
• 2-[(2-carboxyphenyl)disulfanyl]benzoic acid

3-piperazin-1-yl-1,2-benzothiazole Preparation Products

• 3-piperazin-1-yl-1,2-benzothiazole (87691-87-0)

• 1. An integrated process of CO2 capture and in situ hydrogenation to formate using a tunable ethoxyl-functionalized amidine and Rh/bisphosphine system?
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Introduction to 3-piperazin-1-yl-1,2-benzothiazole (CAS No. 87691-87-0)

3-piperazin-1-yl-1,2-benzothiazole, identified by its Chemical Abstracts Service (CAS) number 87691-87-0, is a heterocyclic compound that has garnered significant attention in the field of pharmaceutical and medicinal chemistry. This compound belongs to the benzothiazole class, a scaffold widely recognized for its biological activity and structural versatility. The presence of a piperazine moiety in its structure enhances its pharmacological potential, making it a valuable candidate for further investigation in drug discovery and development.

The structural composition of 3-piperazin-1-yl-1,2-benzothiazole consists of a benzothiazole ring system linked to a piperazine group. The benzothiazole moiety is known for its ability to interact with various biological targets, including enzymes and receptors, while the piperazine nitrogen atoms provide opportunities for hydrogen bonding and salt formation, which are critical for drug-like properties such as solubility and bioavailability.

In recent years, there has been a surge in research focused on developing novel therapeutic agents derived from benzothiazole derivatives. The combination of the benzothiazole and piperazine functionalities in 3-piperazin-1-yl-1,2-benzothiazole positions it as a promising lead compound for addressing a range of therapeutic challenges. Studies have demonstrated the potential of this compound in modulating biological pathways associated with inflammation, neurodegeneration, and infectious diseases.

One of the most compelling aspects of 3-piperazin-1-yl-1,2-benzothiazole is its ability to serve as a versatile building block for more complex molecules. Medicinal chemists have leveraged its scaffold to design derivatives with enhanced potency and selectivity. For instance, modifications at the piperazine nitrogen atoms can fine-tune pharmacokinetic properties, while alterations at the benzothiazole ring can optimize interactions with biological targets.

Recent advancements in computational chemistry have accelerated the process of identifying promising candidates like 3-piperazin-1-yl-1,2-benzothiazole. Molecular docking studies have revealed its potential binding affinity to various protein targets, including kinases and transcription factors. These insights have guided experimental efforts toward optimizing its pharmacological profile.

The synthesis of 3-piperazin-1-yl-1,2-benzothiazole involves multi-step organic reactions that require careful optimization to ensure high yield and purity. Common synthetic routes include nucleophilic substitution reactions at the benzothiazole ring followed by functionalization of the piperazine moiety. Advances in synthetic methodologies have enabled more efficient and scalable production processes, making it feasible to conduct extensive biological evaluations.

In preclinical studies, 3-piperazin-1-yl-1,2-benzothiazole has shown encouraging results in models of inflammation and neuroprotection. Its ability to inhibit key inflammatory mediators has made it a candidate for treating chronic inflammatory disorders. Additionally, its neuroprotective effects have been observed in models of neurodegenerative diseases, suggesting potential therapeutic applications in conditions such as Alzheimer's and Parkinson's disease.

The pharmacokinetic profile of 3-piperazin-1-yl-1,2-benzothiazole is another area of active investigation. Initial studies indicate that it exhibits moderate solubility in water and favorable metabolic stability, which are crucial factors for drug development. However, further optimization may be required to enhance its bioavailability and prolong its half-life in vivo.

One notable feature of 3-piperazin-1-yl-1,2-benzothiazole is its potential to act as a prodrug or precursor for more active metabolites. This property could be exploited to improve drug delivery systems and enhance therapeutic efficacy. Researchers are exploring various strategies to harness this potential, including chemical modifications that facilitate metabolic activation.

The future directions for research on 3-piperazin-1-yl-1,2-benzothiazole include exploring its interactions with novel biological targets and evaluating its efficacy in clinical trials. Collaborative efforts between academic institutions and pharmaceutical companies are essential to translate preclinical findings into tangible therapeutic benefits.

In conclusion,3-piperazin-1-ylil,2-benzothiazole (CAS No. 87691-87-0) represents a promising compound with significant therapeutic potential. Its unique structural features and demonstrated biological activity make it an attractive candidate for further development in pharmaceutical research. As our understanding of disease mechanisms continues to evolve,3-piperazin-1-ylil,2-benzothiazole may play a crucial role in addressing some of today's most pressing medical challenges.

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