21504-96-1

Basic information

• Product Name: N-CYANO-S-METHYL-N'PHENYLISOTHIOUREA
• Synonyms: N-CYANO-S-METHYL-N'PHENYLISOTHIOUREA;methyl N'-cyano-N-phenylimidothiocarbamate;N-cyano-1-(methylthio)-N'-phenylformamidine;N-cyano-1-(methylthio)-N'-phenyl-formamidine;N-cyano-1-methylsulfanyl-N'-phenyl-formamidine;N-cyano-1-methylsulfanyl-N'-phenylmethanimidamide;N-cyano-1-methylsulfanyl-N'-phenyl-methanimidamide
• CAS NO: 21504-96-1
• Molecular Formula: C₉H₉N₃S
• Molecular Weight: 191.25
• Mol File: 21504-96-1.mol

Chemical Properties

• Melting Point: 185 °C
• Appearance: /
• CAS DataBase Reference: N-CYANO-S-METHYL-N'PHENYLISOTHIOUREA(CAS DataBase Reference)
• NIST Chemistry Reference: N-CYANO-S-METHYL-N'PHENYLISOTHIOUREA(21504-96-1)
• EPA Substance Registry System: N-CYANO-S-METHYL-N'PHENYLISOTHIOUREA(21504-96-1)

Safety Data

• Hazardous Substances Data: 21504-96-1(Hazardous Substances Data)

Upstream product

• 62-53-3 aniline 
• 10191-60-3 dimethyl N-cyanodithioiminocarbonate 
• 74-88-4 methyl iodide 

Downstream Products

• 24010-78-4 N-Phenyl-N'-cyano-O-methylisoureid 
• 60178-50-9 1-[3-(4-chloro-phenyl)-[1,2,4]oxadiazol-5-yl]-2-methyl-3-phenyl-isothiourea 
• 41410-39-3 N'-cyano-N-phenylguanidine 
• 55988-11-9 1,1,1,3,3,3-hexafluoro-2-(4-methylsulfanyl-5-phenyl-6,6-bis-trifluoromethyl-5,6-dihydro-[1,3,5]oxadiazin-2-ylideneamino)-propan-2-ol 
• 60178-49-6 2-methyl-1-[3-(3-nitro-phenyl)-[1,2,4]oxadiazol-5-yl]-3-phenyl-isothiourea 
• 3310-68-7 N³-phenyl-1H-1,2,4-triazole-3,5-diamine 
• 74-93-1 methylthiol 
• 79183-80-5 4-imino-2-phenylamino-4,5-dihydrothiazole 
• 75565-34-3 N⁵-Phenyl-[1,2,4]oxadiazole-3,5-diamine 
• 75564-41-9 5-amino-3-aminophenyl-1,2,4-oxadiazole 
• 37634-00-7 1-methyl-N⁵-phenyl-1H-[1,2,4]triazole-3,5-diamine 
• 106580-57-8 1-methyl-3-phenylamino-5-amino-1H-1,2,4-triazole 
• 858640-92-3 C₁₅H₂₈N₄OSSi₂ 
• 75592-11-9 N-cyano-N'-phenyl-N,Ndimethylguanidine 

Relevant articles and documents

Syntheses and Crystal Structures of Methyl N-Substituted-N′-Cyanocarbamimidothioates Derived from Dimethyl N-Cyanodithioiminocarbonate

Abstract: Reaction of dimethyl N-cyanodithioiminocarbonate and arylamine or alkylamine compounds in the refluxing ethanol solution afforded the according methyl N-substituted-N′-cyanocarbamimidothioates 1–16 in good yields. Compounds 1–16 were characterized by proton nuclear magnetic resonance (1H NMR) and infrared spectroscopies, of which the structures of compounds 1, 2 and 3 (Elgemeie et al. in Acta Cryst E71:104–111, 2015) were established by X-ray crystallography, showing that weak hydrogen-bonding interactions exist in compounds 1–3. Compound 1 crystallizes in the orthorhombic space group Pbca, with a = 6.997(2), b = 7.395(2), c = 36.112(11) ?, and Z = 8. The unit cell of 2 has a monoclinic P21/c symmetry with the cell parameters a = 5.8717(12), b = 4.6598(9), c = 37.799(9) ?, β = 91.126(6)°, and Z = 4. Compound 3 crystallizes in the orthorhombic space group Pbca, with a = 7.123(3), b = 7.374(3), c = 38.538(16) ?, and Z = 8. Graphic Abstract: A series of methyl N-subsituted-N′-cyanocarbamimidothioate compounds were efficiently synthesized via the reaction of arylamine or alkylamine compounds with dimethyl N-cyanodithioiminocarbonate. The structures of compounds 1–3 were characterized by X-Ray crystallography.[Figure not available: see fulltext.]

Acylated 1 H-1,2,4-Triazol-5-Amines Targeting Human Coagulation Factor XIIa and Thrombin: Conventional and Microscale Synthesis, Anticoagulant Properties, and Mechanism of Action

We herein report the conventional and microscale parallel synthesis of selective inhibitors of human blood coagulation factor XIIa and thrombin exhibiting a 1,2,4-Triazol-5-Amine scaffold. Structural variations of this scaffold allowed identifying derivative 21i, a potent 29 nM inhibitor of FXIIa, with improved selectivity over other tested serine proteases and also finding compound 21m with 27 nM inhibitory activity toward thrombin. For the first time, acylated 1,2,4-Triazol-5-Amines were proved to have anticoagulant properties and the ability to affect thrombin-And cancer-cell-induced platelet aggregation. Performed mass spectrometric analysis and molecular modeling allowed us to discover previously unknown interactions between the synthesized inhibitors and the active site of FXIIa, which uncovered the mechanistic details of FXIIa inhibition. Synthesized compounds represent a promising starting point for the development of novel antithrombotic drugs or chemical tools for studying the role of FXIIa and thrombin in physiological and pathological processes.

Inhibition of Copper Corrosion with N-Arylaminotriazoles in Aqueous Chloride Solutions and in Air

Abstract: A series of 3-(N-arylamino)-5-amino-1Н-1,2,4-triazoles were prepared by the reaction of S,S-dimethyl cyanodithioimidocarbamate with appropriate anilines. The inhibiting effect of the products on the corrosion of copper of M1 grade in acidic and neutral chloride-containing media was studied using electrochemical and accelerated electroless methods. The maximal degree of protection ensured by commercially available 3,5-diamino-1H-1,2,4-triazole and the synthesized 3-phenylamino, 3-(4-methylphenylamino), 3-(4-chlorophenylamino), and 3-(3-chlorophenylamino) derivatives of 5-amino-1Н-1,2,4-triazole reaches 70–87%. In acid solutions, the synthesized compounds show higher performance than the 3,5-diamino derivative, ensuring up to 92–96% protection. Similar results were obtained in experiments in a salt fog chamber.

Nicotinamide phosphoribosyltransferase inhibitors, design, preparation, and structure-activity relationship

Existing pharmacological inhibitors for nicotinamide phosphoribosyltransferase (NAMPT) are promising therapeutics for treating cancer. By using medicinal and computational chemistry methods, the structure-activity relationship for novel classes of NAMPT inhibitors is described, and the compounds are optimized. Compounds are designed inspired by the NAMPT inhibitor APO866 and cyanoguanidine inhibitor scaffolds. In comparison with recently published derivatives, the new analogues exhibit an equally potent antiproliferative activity in vitro and comparable activity in vivo. The best performing compounds from these series showed subnanomolar antiproliferative activity toward a series of cancer cell lines (compound 15: IC50 0.025 and 0.33 nM, in A2780 (ovarian carcinoma) and MCF-7 (breast), respectively) and potent antitumor in vivo activity in well-tolerated doses in a xenograft model. In an A2780 xenograft mouse model with large tumors (500 mm3), compound 15 reduced the tumor volume to one-fifth of the starting volume at a dose of 3 mg/kg administered ip, bid, days 1-9. Thus, compounds found in this study compared favorably with compounds already in the clinic and warrant further investigation as promising lead molecules for the inhibition of NAMPT.

A one-pot, three-component, microwave-promoted synthesis of 2-amino-substituted 7-amino-1,2,4-triazolo[1,5-a][1,3,5]triazines

A new, efficient, catalyst-free, one-pot, three-component method for the synthesis of 2-amino-substituted 7-amino-1,2,4-triazolo[1,5-a][1,3,5]triazines using 3,5-diamino-1,2,4-triazoles, cyanamide, and triethyl orthoformate is developed. The reaction proceeds smoothly under microwave-assisted heating. Advantages of the method include using easily available reagents, short reaction times, and operational simplicity.

Imidazole Derivatives for the Treatment of Gastrointestinal Disorders

The present invention relates to novel compounds having a positive allosteric GABAB receptor (GBR) modulator effect, methods for the preparation of said compounds and to their use, optionally in combination with a GABAB agonist, for

GABA-B RECEPTOR MODULATORS

The present invention relates to novel imidazole derivatives having a positive allosteric GABAB receptor (GBR) modulator effect, methods for the preparation of said compounds and to their use, optionally in combination with a GABAB a

IMIDAZOLE DERIVATIVES FOR THE TREATMENT OF GASTROINTESTINAL DISORDERS

The present invention relates to novel imidazole derivatives having a positive allosteric GABAB receptor (GBR) modulator effect, methods for the preparation of said compounds and to their use, optionally in combination with a GABAB agonist, for the inhibi

Regioselective preparation of N-substituted 3,5-diamino-1,2,4-oxadiazoles

Regioselective preparation of 3,5-diamino-1,2,4-oxadiazoles which have a substituent on one or the other amino group has been developed. When 1-substituted 3-cyano-2-ethylisourea (2) was allowed to react with hydroxylamine under basic conditions, 5-amino-3-(substituted amino)-1,2,4-oxadiazole (3) was obtained in good yield. On the other hand, 3-amino-5-(substituted amino)-1,2,4-oxadiazoles (4), a regioisomer of 3, could be synthesized by the reaction of N,O-bis(trimethylsilyl)hydroxylamine (9) with 2 or 1-substituted 3-cyano-2-methylisothiourea (1) and subsequent alcoholysis.

DIAMINOTHIAZOLES AND DIAMINOTHIOPHENES

Several 2,4-diaminothiazoles and 2,4-diaminothiophenes could be easily obtained by metallation using LDA from aminomethylthiomethylenecyanamides 2 and aminomethylthiomethylenemalononitrile, respectively.