116567-17-0

Basic information

• Product Name: N-(3-BROMOPHENYL)HYDRAZINECARBOTHIOAMIDE
• Synonyms: Hydrazinecarbothioamide, N-(3-bromophenyl)-
• CAS NO: 116567-17-0
• Molecular Formula: C₇H₈BrN₃S
• Molecular Weight: 246.13
• Mol File: 116567-17-0.mol

Chemical Properties

• Melting Point: 141-142 °C
• Boiling Point: 333.7°Cat760mmHg
• Flash Point: 155.6°C
• Appearance: /
• Density: 1.726g/cm³
• Vapor Pressure: 0.000135mmHg at 25°C
• Refractive Index: 1.748
• PKA: 10.26±0.70(Predicted)
• CAS DataBase Reference: N-(3-BROMOPHENYL)HYDRAZINECARBOTHIOAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(3-BROMOPHENYL)HYDRAZINECARBOTHIOAMIDE(116567-17-0)
• EPA Substance Registry System: N-(3-BROMOPHENYL)HYDRAZINECARBOTHIOAMIDE(116567-17-0)

Safety Data

• Hazardous Substances Data: 116567-17-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H8BrN3S/c8-5-2-1-3-6(4-5)10-7(12)11-9/h1-4H,9H2,(H2,10,11,12)

Upstream product

• 2131-59-1 3-bromophenyl isothiocyanate 
• 591-19-5 m-Bromoaniline 
• 56356-83-3 (3-bromo-phenyl)-dithiocarbamic acid 

Downstream Products

• 27551-12-8 (3-bromo-phenyl)-(5-methyl-[1,3,4]thiadiazol-2-yl)-amine 
• 1036761-91-7 (3-bromo-phenyl)-[1,3,4]thiadiazol-2-yl-amine 
• 1084892-91-0 5-methyl-1H-indole-2,3-dione 3-[N-(3-bromophenyl)thiosemicarbazone] 
• 1084893-15-1 1,5-dimethyl-1H-indole-2,3-dione 3-[N-(3-bromophenyl)thiosemicarbazone] 
• 1192927-62-0 2-acetyl-N-(3-bromophenyl)hydrazinecarbothioamide 
• 1221255-91-9 N-(3-bromophenyl)-2-(quinolin-2-ylmethylene)hydrazinecarbothioamide 
• 1282612-24-1 C₃₉H₅₀Br₂N₆O₂S₂ 
• 1332478-54-2 methyl (5β)-3-[2-[[(3-bromophenyl)amino]thioxomethyl]hydrazinylidene]-12-oxocholan-24-oate 
• 1398501-19-3 N-(3-bromophenyl)-2-(5-chloro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)-1-hydrazinecarbothioamide 
• 1369482-99-4 C₂₂H₁₉BrN₄S 

Relevant articles and documents

Thiosemicarbazone-based lead optimization to discover high-efficiency and low-toxicity anti-gastric cancer agents

In this paper, a series of thiosemicarbazone derivatives containing different aromatic heterocyclic groups were synthesized and the tridentate donor system of the lead compound was optimized. Most of the target compounds showed improved antiproliferative activity against MGC803 cells. SAR studies revealed that compound 5d displayed significant advantages in inhibition effect with an IC50 value of 0.031 μM, and better selectivity between cancer and normal cells than 3-AP and DpC (about 15- and 5-fold improved respectively). Besides, compound 5d showed selective antiproliferative activity in not only other cancer cells but also different gastric cancer cell lines. In-depth mechanism studies showed that compound 5d could induce mitochondria-related apoptosis which might be related to the elevation of intracellular ROS level, and cause cell cycle arrest at S phase. Moreover, 5d could evidently suppress the cell migration and invasion by blocking the EMT (epithelial–mesenchymal transition) process. Consequently, our studies provided a lead optimization strategy of thiosemicarbazone derivatives which would contribute to discover high-efficiency and low-toxicity agents for the treatment of gastric cancer.

A thiourea structure unit including shrinking amino aromatic compound and its preparation method and application (by machine translation)

The invention relates to the technical field of pharmaceutical chemistry, and in particular relates to a thiourea structure unit including shrinking amino aromatic compound and its preparation method and application. The present invention provides including shrinking amino thiourea structure unit of the aromatic heterocyclic compound with the gastric cancer cells through the inner metal ion chelating form stable complexes, thereby suppressing the MGC803 gastric cancer cell proliferation activity. The results of the embodiment of the display, and the compound 3 - AP compared with, the present invention provides including shrinking amino thiourea structure unit of the aromatic heterocyclic compound to stomach MGC803 has better proliferation inhibitory activity. (by machine translation)

Thiosemicarbazide, a fragment with promising indolamine-2,3-dioxygenase (IDO) inhibition properties

With the aim to explore the interest of the thiosemicarbazide scaffold for the inhibition of the indoleamine 2,3-dioxygenase (IDO), a promising therapeutic target for anticancer immunotherapy, a series of 32 phenylthiosemicarbazide derivatives was prepared and their IDO inhibition evaluated. Our study demonstrated that among these derivatives, compound 14 characterized with a 4-cyanophenyl group on the thiosemicarbazide was the more potent IDO inhibitor in this series being endowed with an IC50 of 1.2 μM. The SAR depicted showed that substitution in the 3- and 4-position relative to the phenylthiosemicarbazide are very promising whereas substitution in the 2-position always leads to less potent or inactive derivatives. In fact the study highlighted a novel interesting scaffold for IDO inhibition for further development.

Synthesis of new hyodeoxycholic acid thiosemicarbazone derivatives under solvent-free conditions using microwave

An efficient and simple method for synthesis of new hyodeoxycholic acid thiosemicarbazone derivatives under solvent-free conditions using microwave has been developed. Its main advantages are short reaction times, good conversions and the environmentally friendly nature of the process. The preliminary results indicate that some of these compounds possess inhibitory effects against E. coli.

Synthesis of novel alkoxycarbonyl thiosemicarbazide molecular tweezers derived from deoxycholic acid under microwave irradiation

A series of novel 12α-alkoxycarbonyl thiosemicarbazide molecular tweezers based on 3α-(1-naphthoyl) deoxycholic acid methyl ester were synthesised under microwave irradiation. Their structures were characterised by 1H NMR, IR, MS spectra and elemental analysis. Their chiral recognition properties for the methyl esters of amino acids were investigated. The preliminary results showed that these molecular tweezers have good enantioselective recognition for D/L-amino acid methyl esters.

A series of α-heterocyclic carboxaldehyde thiosemicarbazones inhibit topoisomerase IIα catalytic activity

A series of novel thiosemicarbazone derivatives bearing condensed heterocyclic carboxaldehyde moieties were designed and synthesized. Among them, TSC24 exhibited broad antiproliferative activity in a panel of human tumor cells and suppressed tumor growth in mice. The mechanism research revealed that TSC24 was not only an iron chelator but also a topoisomerase IIα catalytic inhibitor. Its inhibition on topoisomerase IIα was due to direct interaction with the ATPase domain of topoisomerase IIα which led to the block of ATP hydrolysis. Molecular docking predicted that TSC24 might bind at the ATP binding site, which was confirmed by the competitive inhibition assay. These results about the mechanisms involved in the anticancer activities of thiosemicarbazones will aid in the rational design of novel topoisomerase II-targeted drugs and will provide insights into the discovery and development of novel cancer therapeutics based on the dual activity to chelate iron and to inhibit the catalytic activity of topoisomerase IIα.

N-(Acetamido)thiourea based simple neutral hydrogen-bonding receptors for anions

N-(Acetamido)-N′-phenylthioureas (4-6) were found to be efficient anion receptors with higher anion affinity than their N-benzamido-N′- phenylthiourea counterparts (1 and 2). The N′-phenylthiourea moiety in 4-6 was shown to be the chromophore with an absorption maximum at ca. 270 nm. It was found that, in the presence of anions, the absorption at ca. 270 nm of 4-6 (except 5f) in acetonitrile (MeCN) was blue shifted and enhanced while a red-shifted shoulder appeared at ca. 295 nm, together with an isosbestic point at ca. 240 nm. The 1:1 anion binding constants of 4-6, for example at 10 6-107 M-1 order of magnitude for AcO - in MeCN, were found to be higher than those of 1 and 2, although the acidity of the thioureido -NH protons in 4-6 is lower than that in 1 and 2. 1H NMR data indicates that the N-N single bond in 4-6 is twisted but less than that in 1 and 2. A conformation change at the N-N single bond of 4-6 was suggested to occur upon anion binding which leads to a planar hydrogen-bonding network in the anion binding complex in which a charge transfer takes place with the N-acyl moiety being the electron acceptor. Variations in the CD signals of a proline derivative 6 bearing a chiral center in the N-amido moiety provide direct evidence for this conformation change upon its binding with anions in MeCN. The amplified effect of substituent X at the N′-phenyl ring of 5 on the anion binding constant supports the conclusion of anion-binding switched charge transfer in the anion binding complex. 1H NMR and absorption titrations for 5 indicated that the anion-receptor interaction was of a hydrogen-bonding nature until the N′-phenyl substituent X is as electron-withdrawing as m-CF3 (5e). With X being the more electron-withdrawing p-NO2 (5f), deprotonation of the thioureido -NH occurs in the presence of anion. Results reported here confirm that N-amidothioureas derived from both N-aliphatic and N-aromatic amides can in general be a family of efficient hydrogen-bonding receptors, with the aliphatic N-amido derivatives being more efficient. This provides a wider structural diversity for designing thiourea-based functional molecules such as anion receptors and organocatalysts. Preliminary experiments confirm that 6 could catalyse efficiently the reduction of nitrostyrene in CH2Cl2 and MeCN.

NEW COMPOUNDS

The invention relates to new bicyclic heterocyclic derivative compounds, to pharmaceutical compositions comprising said compounds and to the use of said compounds in the treatment of diseases, e.g. cancer.

Synthesis and antituberculosis activity of 5-methyl/trifluoromethoxy-1H-indole-2,3-dione 3-thiosemicarbazone derivatives

New series of 5-methyl/trifluoromethoxy-1H-indole-2,3-dione 3-thiosemicarbazones 3a-t, 1-methyl-5-methyl/trifluoromethoxy-1H-indole-2,3-dione 3-thiosemicarbazones 4a-y and 5-trifluoromethoxy-1-morpholinomethyl-1H-indole-2,3-dione 3-thiosemicarbazones 5a-m were synthesized. The structures of the synthesized compounds were confirmed by spectral data and elemental analysis. The new 5-methyl/trifluoromethoxy-1H-indole-2,3-dione derivatives, along with previously synthesized 5-methyl-1H-indole-2,3-dione 3-thiosemicarbazones 6a-l, were evaluated for in vitro antituberculosis activity against Mycobacterium tuberculosis H37Rv. 5-Methyl-1H-indole-2,3-dione 3-thiosemicarbazones (3b, 3d, 3f, 6c, 6d, and 6f), 5-trifluoromethoxy-1H-indole-2,3-dione 3-thiosemicarbazones (3q-s) and 5-trifluoromethoxy-1-morpholinomethyl-1H-indole-2,3-dione 3-thiosemicarbazones (5e and 5j-l) were found to be the most potent inhibitors of M. tuberculosis growth described in this study.