21048-05-5

Basic information

• Product Name: Thiobenzoic acid 1-methylhydrazide
• Synonyms: N-Methyl-N-thiobenzoylhydrazine;Thiobenzoic acid 1-methylhydrazide;thiobenzoic acid N-Methyl-hydrazide, thiobenzoic acid-(N'-Methyl-hydrazide)
• CAS NO: 21048-05-5
• Molecular Formula: C₈H₁₀N₂S
• Molecular Weight: 166.24
• Mol File: 21048-05-5.mol

Chemical Properties

• Melting Point: 89-91 ºC
• Boiling Point: 267 ºC
• Flash Point: 115 ºC
• Appearance: /
• Density: 1.189
• PKA: 1.16±0.18(Predicted)
• CAS DataBase Reference: Thiobenzoic acid 1-methylhydrazide(CAS DataBase Reference)
• NIST Chemistry Reference: Thiobenzoic acid 1-methylhydrazide(21048-05-5)
• EPA Substance Registry System: Thiobenzoic acid 1-methylhydrazide(21048-05-5)

Safety Data

• Hazardous Substances Data: 21048-05-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Thiobenzoic acid 1-methylhydrazide is used as an intermediate in the synthesis of various pharmaceuticals for its ability to react with different functional groups, contributing to the development of new drugs with diverse therapeutic properties.
Used in Agricultural Chemical Industry:
In the agricultural chemical industry, Thiobenzoic acid 1-methylhydrazide is used as an intermediate in the production of various agrochemicals, such as pesticides and herbicides, due to its reactivity and potential to form active ingredients with pest control properties.
Used in Dye Industry:
Thiobenzoic acid 1-methylhydrazide is utilized as an intermediate in the synthesis of dyes, where its chemical structure allows for the creation of colorants with specific properties, such as colorfastness and brightness.
Used in Material Science:
Thiobenzoic acid 1-methylhydrazide is employed in the development of new materials and organic syntheses, where its unique chemical properties can be leveraged to create innovative materials with specialized applications in various industries.
Used in Research and Development:
In research and development, Thiobenzoic acid 1-methylhydrazide serves as a valuable compound for exploring new chemical reactions and syntheses, potentially leading to the discovery of novel compounds with unique properties and applications.

Upstream product

• 302-15-8 methylhydrazine sulfuric acid 
• 942-91-6 Carboxymethyl dithiobenzoate 
• 108-86-1 bromobenzene 
• 7439-95-4 magnesium dihydride 
• 15563-40-3 N-thiobenzoylpiperidine 
• 1189371-78-5 tert-butyl 2-methyl-2-(phenylcarbonothioyl)hydrazinecarboxylate 
• 60-34-4 methylhydrazine 
• 50-00-0 formaldehyd 
• 100-58-3 phenylmagnesium bromide 
• 100-52-7 benzaldehyde 
• 1483-24-5 1-methyl-1-benzoylhydrazine 
• 98-88-4 benzoyl chloride 

Downstream Products

• 37764-95-7 5-benzoylamino-3-methyl-2-phenyl-[1,3,4]thiadiazolium betaine 
• 488832-69-5 elesclomol 
• 1224195-72-5 Cu(II)-elesclomol 
• 1224195-73-6 Ni(II)-elesclomol 
• 39736-90-8 5-acetylamino-3-methyl-2-phenyl-[1,3,4]thiadiazolium betaine 
• 39736-93-1 3-methyl-5-(4-nitro-benzoylamino)-2-phenyl-[1,3,4]thiadiazolium betaine 
• 34257-17-5 5-anilino-3-methyl-2-phenyl-[1,3,4]thiadiazolium; chloride 
• 37764-89-9 5-anilino-3-methyl-2-phenyl-[1,3,4]thiadiazolium; acetate 
• 39736-91-9 5-(2,2-dimethyl-propionylamino)-3-methyl-2-phenyl-[1,3,4]thiadiazolium betaine 
• 37067-45-1 N-methyl-N-(α-methylsulfanyl-benzylidene)-hydrazinium; iodide 
• 20185-01-7 benzaldehyde methylthiobenzoylhydrazone 
• 488832-79-7 2-butyl-N′¹,N′³-dimethyl-N′¹,N′³-bis(phenylcarbonothioyl)malonohydrazide 
• 488832-76-4 N′¹,N′³,2-Trimethyl-N′¹,N′³-bis(phenylcarbonothioyl)malonohydrazide 
• 1228789-28-3 C₁₀H₁₁ClN₂O₃S₂ 

Relevant articles and documents

Paclitaxel enhancer compounds

Disclosed is a compound represented by the Structural Formula (I): Y is a covalent bond, a phenylene group or a substituted or unsubstituted straight chained hydrocarbyl group. In addition, Y, taken together with both >C═Z groups to which it is bonded, is a substituted or unsubstituted aromatic group. Preferably, Y is a covalent bond or —C(R7R8)—. R1 and R2 are independently an aryl group or a substituted aryl group, R3 and R4 are independently —H, an aliphatic group, a substituted aliphatic group, an aryl group or a substituted aryl group. R5-R6 are independently —H, an aliphatic group, a substituted aliphatic group, an aryl group or a substituted aryl group. R7 and R8 are each independently —H, an aliphatic or substituted aliphatic group, or R7 is —H and R8 is a substituted or unsubstituted aryl group, or, R7 and R8, taken together, are a C2-C6 substituted or unsubstituted alkylene group. Z is ═O or ═S. Also disclosed are pharmaceutical compositions comprising the compound of the present invention and a pharmaceutically acceptable carrier or diluent. Also disclosed is a method of treating a subject with cancer by administering to the subject a compound of Structural Formula (I) in combination with Paclitaxel or an analog of Paclitaxel.

Molecular mechanisms of the biological activity of the anticancer drug elesclomol and its complexes with Cu(II), Ni(II) and Pt(II)

The bis(thiohydrazide) amide elesclomol has extremely potent antiproliferative activity and is currently in clinical trials as an anticancer agent. Elesclomol strongly binds copper and may be exerting its cell growth inhibitory effects by generating copper-mediated oxidative stress. Nickel(II) and platinum(II) complexes of elesclomol were synthesized and characterized in order to investigate if these biologically redox inactive metal complexes could also inhibit cell growth. The nickel(II)-elesclomol and platinum(II) elesclomol complexes were 34- and 1040-fold less potent than the copper(II)-elesclomol complex towards human leukemia K562 cells. These results support the conclusion that a redox active metal is required for elesclomol to exert its cell growth inhibitory activity. Copper(II)-elesclomol was also shownto efficiently oxidize ascorbic acid at physiological ascorbic acid concentrations. Reoxidation of the copper(I) thus produced would lead to production of damaging reactive oxygen species. An X-ray crystallographic structure determination of copper(II)-elesclomol showed that it formed a 1:1 neutral complex with a distorted square planar structure. The kinetics and equilibria of the competition reaction of the strong copper(II) chelator TRIEN with copper(II)-elesclomol were studied spectrophotometrically under physiological conditions. These results showed elesclomol bound copper(II) with a conditional stability constant 24-fold larger than TRIEN. A log stability constant of 24.2 was thus indirectly determined for the copper(II)-elesclomol complex.

Syntheses and antitumor activities of N′1, N′3-dialkyl-N′1,N′3-di- (alkylcarbonothioyl) malonohydrazide: The discovery of elesclomol

A series of N′1,N′3-dialkyl- N′1,N′3-di(alkylcarbonothioyl) malonohydrazides have been designed and synthesized as anticancer agents by targeting oxidative stress and Hsp70 induction. Structure-activity relationship (SAR) studies lead to the discovery of STA-4783 (elesclomol), a novel small molecule that has been evaluated in a number of clinical trials as an anticancer agent in combination with Taxol.

PROCESS FOR PREPARING BIS(THIOHYDRAZIDE AMIDES)

Disclosed herein are methods of preparing a bis(thio-hydrazide amides) compounds of the following structural formula: wherein R1, R2, R3, R4, R5, R6 and R13 are defined herein.

PROCESS FOR PREPARING BIS(THIOHYDRAZIDE AMIDES)

Disclosed herein are methods of preparing a bis(thio-hydrazide amides) compounds of the following structural formula (I), wherein R1., R3 and Y are defined herein.

Purification of bis (thiohydrazide amides)

Disclosed herein are methods of purifying a bis(thio-hydrazide amides) compounds of the following structural formula: wherein R1, R2, R3, R4, R7, R8, Z, and Y are defined herein.

Taxol enhancer compounds

Disclosed is a compound represented by the Structural Formula (I): Y is a covalent bond, a phenylene group or a substituted or unsubstituted straight chained hydrocarbyl group. In addition, Y, taken together with both >C═Z groups to which it is bonded, is a substituted or unsubstituted aromatic group. Preferably, Y is a covalent bond or —C(R7R8)—.R1 and R2 are independently an aryl group or a substituted aryl group, R3 and R4 are independently —H, an aliphatic group, a substituted aliphatic group, an aryl group or a substituted aryl group.R5-R6 are independently —H, an aliphatic group, a substituted aliphatic group, an aryl group or a substituted aryl group.R7 and R8 are each independently —H, an aliphatic or substituted aliphatic group, or R7 is —H and R8 is a substituted or unsubstituted aryl group, or, R7 and R8, taken together, are a C2-C6 substituted or unsubstituted alkylene group.Z is ═O or ═S. Also disclosed are pharmaceutical compositions comprising the compound of the present invention and a pharmaceutically acceptable carrier or diluent. Also disclosed is a method of treating a subject with cancer by administering to the subject a compound of Structural Formula (I) in combination with taxol or an analog of taxol.

Taxol enhancer compounds

Disclosed is a compound represented by the Structural Formula (I): Y is a covalent bond, a phenylene group or a substituted or unsubstituted straight chained hydrocarbyl group. In addition, Y, taken together with both >C═Z groups to which it is bonded, is a substituted or unsubstituted aromatic group. Preferably, Y is a covalent bond or —C(R7R8)—. R1 and R2 are independently an aryl group or a substituted aryl group, R3 and R4 are independently —H, an aliphatic group, a substituted aliphatic group, an aryl group or a substituted aryl group. R5-R6 are independently —H, an aliphatic group, a substituted aliphatic group, an aryl group or a substituted aryl group. R7 and R8 are each independently —H, an aliphatic or substituted aliphatic group, or R7 is —H and R8 is a substituted or unsubstituted aryl group, or, R7 and R8, taken together, are a C1-C6 substituted or unsubstituted alkylene group. Z is ═O or ═S. Also disclosed are pharmaceutical compositions comprising the compound of the present invention and a pharmaceutically acceptable carrier or diluent. Also disclosed is a method of treating a subject with cancer by administering to the subject a compound of Structural Formula (I) in combination with taxol or an analog of taxol.