4-(2-Morpholinoethyl)-3-thiosemicarbazide
[CAS# 77644-45-2]

Identification

• Classification: Organic raw materials >> Organic derivative of hydrazine or hydrazine
• Name: 4-(2-Morpholinoethyl)-3-thiosemicarbazide
• Synonyms: 1-amino-3-(2-morpholin-4-ylethyl)thiourea
• Molecular Formula: C₇H₁₆N₄OS
• Molecular Weight: 204.29
• CAS Registry Number: 77644-45-2
• EC Number: 673-717-5
• SMILES: C1COCCN1CCNC(=S)NN

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Melting point: 164-168 °C (Decomp.) (Expl.)
• Index of Refraction: 1.572, Calc.^*
• Boiling Point: 340.6±52.0 °C (760 mmHg), Calc.^*
• Flash Point: 159.8±30.7 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

4-(2-Morpholinoethyl)-3-thiosemicarbazide is an organic compound that belongs to the class of thiosemicarbazides, which are widely recognized for their diverse biological and chemical activities. This compound is characterized by the presence of a morpholinoethyl group attached to the nitrogen of a thiosemicarbazide backbone. The thiosemicarbazide structure, featuring a sulfur atom bonded to a nitrogen atom, is a common motif in many bioactive molecules. The addition of a morpholinoethyl group at the fourth position further enhances the compound's properties and introduces potential for various applications in the fields of medicinal chemistry, drug design, and biochemistry.

The discovery of 4-(2-morpholinoethyl)-3-thiosemicarbazide is part of the broader exploration of thiosemicarbazides as a structural class in medicinal chemistry. Thiosemicarbazides and their derivatives have long been studied for their antibacterial, anticancer, and antiviral activities, as well as for their ability to modulate various biochemical pathways. The morpholinoethyl modification is particularly notable for its potential to influence the compound’s ability to cross biological membranes and interact with molecular targets, such as enzymes and receptors. The specific configuration of 4-(2-morpholinoethyl)-3-thiosemicarbazide makes it a promising candidate for development into therapeutic agents with enhanced bioactivity.

One of the primary applications of 4-(2-morpholinoethyl)-3-thiosemicarbazide is in the field of medicinal chemistry, particularly as a potential anticancer agent. Studies have shown that thiosemicarbazides can possess antitumor properties, and modifications to the basic thiosemicarbazide structure can lead to compounds with improved selectivity and potency against cancer cells. The morpholinoethyl group may contribute to the compound's ability to penetrate tumor tissues more effectively, potentially increasing its efficacy as a chemotherapeutic agent. Moreover, some research has indicated that thiosemicarbazides can influence cell cycle regulation and induce apoptosis (programmed cell death) in cancerous cells, which makes them an attractive target for cancer treatment development.

In addition to its anticancer potential, 4-(2-morpholinoethyl)-3-thiosemicarbazide has been explored for its antimicrobial properties. Thiosemicarbazides, in general, have shown activity against a broad spectrum of bacteria and fungi, and derivatives like 4-(2-morpholinoethyl)-3-thiosemicarbazide may offer enhanced antimicrobial action. The compound may function by inhibiting key enzymes or disrupting cellular processes in pathogens, thereby preventing their growth or survival. Its effectiveness against resistant bacterial strains and fungal infections remains an area of active research, as the need for novel antimicrobial agents has grown in the face of increasing resistance to traditional antibiotics.

Beyond its medicinal and antimicrobial applications, 4-(2-morpholinoethyl)-3-thiosemicarbazide has also attracted attention in the field of biochemistry. The compound’s ability to interact with metal ions, such as copper and iron, may offer utility in chelation therapy, where it could be used to manage conditions involving metal overload, such as Wilson's disease or hemochromatosis. Additionally, the thiosemicarbazide structure is known for its role in enzyme inhibition, particularly in the modulation of enzymes involved in metabolic pathways. As such, 4-(2-morpholinoethyl)-3-thiosemicarbazide may hold promise for future research aimed at developing enzyme inhibitors for a variety of diseases, including neurodegenerative disorders and cardiovascular conditions.

The synthesis of 4-(2-morpholinoethyl)-3-thiosemicarbazide typically involves the reaction of thiosemicarbazide with a morpholinoethyl derivative under controlled conditions. This straightforward synthetic approach makes the compound accessible for use in both laboratory research and potential therapeutic applications. However, the bioavailability, stability, and toxicity of the compound in vivo are important factors that need to be thoroughly assessed to determine its suitability for clinical use. These aspects are areas of ongoing study as scientists work to optimize the compound for therapeutic applications.

In conclusion, 4-(2-morpholinoethyl)-3-thiosemicarbazide is a promising thiosemicarbazide derivative with diverse applications in the fields of medicinal chemistry, antimicrobial therapy, and biochemistry. Its potential as an anticancer, antimicrobial, and enzyme-modulating agent makes it a valuable compound for further exploration. Continued research will likely lead to the identification of additional uses and mechanisms of action, potentially contributing to the development of new therapeutic strategies.

References

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