51317-66-9

Usage

Uses

Used in Organic Synthesis:
4-Morpholinophenyl isothiocyanate is used as a reagent in organic synthesis for the introduction of the isothiocyanate functional group into various molecules, which is crucial for the development of new chemical entities with specific properties.
Used in Medicinal Chemistry:
In medicinal chemistry, 4-Morpholinophenyl isothiocyanate is utilized as a reagent to modify molecules, enhancing their biological activity and contributing to the discovery and design of new pharmaceuticals.
Used in the Synthesis of Biologically Active Compounds:
4-Morpholinophenyl isothiocyanate is employed in the synthesis of biologically active compounds, leveraging its ability to introduce the isothiocyanate group to improve the pharmacological properties of these compounds.
Used in Pharmaceutical Development:
4-MORPHOLINOPHENYL ISOTHIOCYANATE is used as a key intermediate in the development of pharmaceuticals, where its incorporation can lead to the creation of drugs with enhanced therapeutic effects.
Used in Antimicrobial and Antifungal Research:
4-Morpholinophenyl isothiocyanate is studied for its potential antimicrobial and antifungal properties, indicating its use in the research and development of new treatments for infectious diseases.
Used in Safety and Toxicity Studies:
Due to its toxic nature, 4-Morpholinophenyl isothiocyanate is also used in safety and toxicity studies to understand its effects on biological systems and to develop methods for safe handling and application in various industries.

InChI:InChI=1/C11H12N2OS/c15-9-12-10-1-3-11(4-2-10)13-5-7-14-8-6-13/h1-4H,5-8H2

Upstream product

• 75-15-0 carbon disulfide 
• 2524-67-6 4-morpholino-4-yl-phenylamine 
• 10389-51-2 1-morpholino-4-nitrobenzene 
• 350-46-9 4-Fluoronitrobenzene 
• 6160-65-2 1,1'-Thiocarbonyldiimidazole 
• 463-71-8 thiophosgene 

Downstream Products

• 883094-24-4 N-(2-hydroxyethyl)-N'-[4-(4-morpholinyl)phenyl]thiourea 
• 903671-54-5 N-cyclopropyl-N'-[4-(4-morpholinyl)phenyl]thiourea 
• 457083-23-7 N-ethyl-N'-[4-(4-morpholinyl)phenyl]thiourea 
• 452949-31-4 N-methyl-N'-[4-(4-morpholinyl)phenyl]thiourea 
• 909871-01-8 4-[4-(morpholin-4-yl)-phenyl]-1-[5-isopropyl-2,4-bis(methoxymethoxy)benzoyl]thiosemicarbazide 
• 909871-22-3 4-[4-(morpholin-4-yl)-phenyl]-1-[5-bromo-2,4-bis(methoxymethoxy)benzoyl]thiosemicarbazide 
• 100891-82-5 C₁₉H₁₉N₅O₂S 
• 1360609-75-1 (4-morpholin-4-yl-phenyl)-[8-(2-phenoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyrazin-2-yl]-amine 
• 1360612-58-3 8-chloro-[1,2,4]triazolo[1,5-a]pyrazin-2-yl-(4-morpholin-4-yl-phenyl)amine 
• 1612875-32-7 2-(furan-2-yl-methylidene)-N-[4-(morpholin-4-yl)phenyl]hydrazine carbothioamide 
• 1612875-33-8 2-(thiophen-2-yl-methylidene)-N-[4-(morpholin-4-yl)phenyl]hydrazinecarbothioamide 
• 1612875-34-9 2-(5-nitrothiophene-2-yl-methylidene)-N-[4-(morpholin-4-yl)phenyl]hydrazine carbothioamide 
• 1612875-35-0 2-(1H-pyrrol-2-yl-methylidene)-N-[4-(morpholin-4-yl)phenyl]hydrazinecarbothioamide 
• 1612875-36-1 2-(4-fluorobenzylidene)-N-[4-(morpholin-4-yl)phenyl]hydrazinecarbothioamide 

Relevant academic research and scientific papers

Discovery of benzo[d]oxazole derivatives as the potent type-I FLT3-ITD inhibitors

Fms-like tyrosine kinase 3 (FLT3) has been considered as a potential drug target for the treatment of acute myeloid leukemia (AML), because of its high and aberrant expression in AML patients, especially the patients with FLT3-ITD mutation. Initiating from a hit compound (IC50: 500 nM against FLT3-ITD), a series of compounds were designed and synthesized based on benzo[d]oxazole-2-amine scaffold to discover new potent FLT3-ITD inhibitors. During the medicinal chemistry works, flexible molecular docking was used to provide design rationale and study the binding modes of the target compounds. Through the mixed SAR exploration based on the enzymatic and cellular activities, compound T24 was identified with potent FLT3-ITD inhibitory (IC50: 0.41 nM) and anti-proliferative (IC50: 0.037 μM against MV4-11 cells) activities. And the binding mode of T24 with “DFG-in” FLT3 was simulated by a 20-ns molecular dynamics run, providing some insights into further medicinal chemistry efforts toward novel FLT3 inhibitors in AML therapy.

Design, computational studies, synthesis and biological evaluation of thiazole-based molecules as anticancer agents

Background: Abolition of cancer warrants effective treatment modalities directed towards specific pathways dysregulated in tumor proliferation and survival. The antiapoptotic Bcl-2 proteins are significantly altered in several tumor types which position them as striking targets for therapeutic intervention. Here we designed, computationally evaluated, synthesized, and biologically tested structurally optimized thiazole-based small molecules as anticancer agents. Methods: The virtually designed 200 molecules were subjected to rigorous docking and in silico ADME-Toxicity studies. Out of this, 23 skeletally diverse thiazole-based molecules which passed pan assay interference compounds (PAINS) filter and were synthetically feasible were synthesized in 3 steps using cheap and readily available reagents. The molecules were in vitro evaluated against Bcl-2-Jurkat, A-431 cancerous cell lines and ARPE-19 cell lines. Molecular Dynamics (MD) simulation studies were performed to analyse conformational changes induced by ligand 32 in Bcl-2. Flow cytometry analysis of compound 32 treated Bcl-2 cells was done to check apoptosis. Results: The molecules exhibited appreciable interactions with Bcl-2 and were having acceptable drug like properties as tested in silico. The multi step synthesis yielded 23 skeletally diverse thiazole-based molecules in up to 80% yield. The molecules simultaneously inhibited Bcl-2 Jurkat cells in vitro without causing detectable toxicity to normal cells (ARPE-19 cells). Among them molecules 32, 50, 53, 57 and 59 showed considerable activities against Bcl-2 Jurkat and A-431cell lines at concentrations ranging from 32–46 μM and 34–52 μM, respectively. The standard doxorubicin exhibited IC50 in Bcl-2 Jurkat and A-431cell lines at 45.87 μM and 42.37 μM, respectively. The molecule 32, almost equipotent in both the cell lines was subjected to molecular dynamics (MD) simulation with Bcl-2 protein (4IEH). It was shown that 32 interacted with protein majorly via hydrophobic interactions and few H-bonding interactions. Fluorescence-activated cell sorting (FACS) analysis established that molecule is dragging cancerous cells towards apoptosis. Discussion and conclusion: The chemical intuition was checked by computation coupled with biological results confirmed that thiazole-based hits have the potential to be developed downstream into potent and safer leads against antiapoptotic Bcl-2 cells.

Synthesis, characterization, and biological evaluation of some novel thiosemicarbazones as possible antibacterial and antioxidant agents

The synthesis and characterization of 18 novel thiosemicarbazones have been investigated as part of a research program on development of compounds with antibacterial and antioxidant activities. Among the tested compounds, 2-(4-hydroxybenzylidene)-N-[4-(tr

8 - SUBSTITUTED 2 -AMINO - [1,2,4] TRIAZOLO [1, 5 -A] PYRAZINES AS SYK TRYROSINE KINASE INHIBITORS AND GCN2 SERIN KINASE INHIBITORS

Compounds of the formula I in which R1, R2 and R4 have the meanings indicated in Claim 1, are inhibitors of Syk, and can be employed, inter alia, for the treatment of cancer, rheumatoid arthritis and / or systemic lupus

Synthesis and biological evaluation of arylthiourea derivatives with antitubercular activity

Tuberculosis (TB) is a contagious disease caused by Mycobacterium tuberculosis (M. tuberculosis), and remains one of the most life-threatening plagues for public health in the world. The emergence of drug resistant strains of TB and co-infection with HIV has further complicated TB treatment. Here, the synthesis and characterizaton of a series of compounds were described, and these were followed by evaluating for their antibacterial activity against M. tuberculosis. Several novel arylthiourea derivatives exhibited excellent activity (lowest MIC=0.09 μg/ml) against M. tuberculosis including drug resistant strains of M. tuberculosis. The results suggest that these compounds are promising candidates for new anti-TB agent development.

TRIAZOLOPYRAZINE DERIVATIVES

Compounds of the formula I in which R1 and R2 have the meanings indicated in Claim 1, are inhibitors of Syk, and can be employed, inter alia, for the treatment rheumatoid arthritis

Isatin-β-thiosemicarbazones as potent herpes simplex virus inhibitors

A series of isatin-β-thiosemicarbazones have been designed and evaluated for antiviral activity against herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2) in a plaque reduction assay. Their cytotoxicity was examined using human rhabdomyosarcoma cells (RD cells). Several derivatives of isatin-β-thiosemicarbazone exhibited significant and selective antiviral activity with low cytotoxicity. It was found that the thiourea group at thiosemicarbazone and the NH functionality at isatin were essential for their antiherpetic activity. The synthesis and structure-activity relationship studies are presented.

Novel derivatives of benzimidazole and imidazo-pyridine and their use as medicaments

A compound of the formula wherein the substituents are as defined in the specification and pharmaceutical salts thereof having a good affinity for sub-types of melanocortin receptors making them useful for treating diseases in which such receptors are included such as pain, inflammatory conditions, etc.

4-Aminothiazole derivatives, their preparation and their use as inhibitors of cyclin-dependent kinases

This invention is directed to aminothiazole compounds of formula (I) wherein R1 is a substituted or unsubstituted group selected from : C1-6-alkyl; C1-6-alkenyl; C1-6-alkynyl; C1-6-alkoxyl; C1-6-alcohol; carbocyclic or heterocyclic, monocyclic or fused or non-fused polycyclic, cycloalkyl; carbocyclic or heterocyclic, monocyclic or fused or non-fused polycyclic, aryl; carbonyl; ether; (C1-6-alkyl)-carbonyl; (C1-6-alkyl)-aryl; (C1-6-alkyl)-cycloalkyl; (C1-6-alkyl)-(C1-6-alkoxyl); aryl-(C1-6-alkoxyl); thioether; thiol; and sulfonyl; wherein when R1 is substituted, each substituent independently is a halogen; haloalkyl; C1-6-alkyl; C1-6-alkenyl; C1-6-alkynyl; hydroxyl; C1-6-alkoxyl; amino; nitro; thiol, thioether; imine; cyano; amido; phosphonato; phosphine; carboxyl; thiocarbonyl; sulfonyl; sulfonamide; ketone; aldehyde; ester; oxygen; carbocyclic or heterocyclic, monocyclic or fused or non-fused polycyclic, cycloalkyl; or carbocyclic or heterocyclic, monocyclic or fused or non-fused polycyclic, aryl; and R2 is a carbocyclic or heterocyclic, monocyclic or fused or non-fused polycyclic, ring structure having a substituent at the position adjacent to the point of attachment, which ring structure is optionally further substituted, where each substituent of R2 independently is a halogen; haloalkyl; C1-6-alkyl; C1-6-alkenyl; C1-6-alkynyl; hydroxyl; C1-6-alkoxyl; amino; nitro; thiol; thioether; imine; cyano; amido; phosphonato; phosphine; carboxyl; thiocarbonyl; sulfonyl; sulfonamide; ketone; aldehyde; ester; oxygen; carbocyclic or heterocyclic, monocyclic or fused or non-fused polycyclic, cycloalkyl; or carbocyclic or heterocyclic, monocyclic or fused or non-fused polycyclic, aryl; or a pharmaceutically acceptable salt of a compound of formula (I), or a prodrug or pharmaceutically active metabolite of a compound of formula (I) or pharmaceutically acceptable salt thereof, for inhibiting cyclin-dependent kinases (CDKs), such as CDK1, CDK2, CDK4, and CDK6. The invention is also directed to the therapeutic or prophylactic use of pharmaceutical compositions containing such compounds and to methods of treating malignancies and other disorders by administering effective amounts of such compounds.