1401006-68-5

Basic information

• Product Name: C₄₅H₅₀N₆O₈S₃
• Synonyms: C₄₅H₅₀N₆O₈S₃
• CAS NO: 1401006-68-5
• Molecular Weight: 899.125
• Mol File: 1401006-68-5.mol

Chemical Properties

• CAS DataBase Reference: C₄₅H₅₀N₆O₈S₃(CAS DataBase Reference)
• NIST Chemistry Reference: C₄₅H₅₀N₆O₈S₃(1401006-68-5)
• EPA Substance Registry System: C₄₅H₅₀N₆O₈S₃(1401006-68-5)

Safety Data

• Hazardous Substances Data: 1401006-68-5(Hazardous Substances Data)

Upstream product

• 5460-29-7 2-(3-bromopropyl)isoindole-1,3-dione 
• 945495-86-3 6-[2-(p-tolylsulfonylamino)ethyl]-3,6,9-triaza-3, 9-p-tolylsulfonyl-1-(2,6)-pyridinecyclodecaphane 
• 7703-74-4 2,6-bis-(bromomethyl)pyridine 
• 98-59-9 p-toluenesulfonyl chloride 
• 4097-89-6 2,2',2''-triaminotriethylamine 
• 98846-92-5 tris[2-(N-tosylaminoethyl)]amine 

Downstream Products

• 1401006-69-6 C₃₇H₄₈N₆O₆S₃ 

Relevant articles and documents

Modulation of DNA binding by reversible metal-controlled molecular reorganizations of scorpiand-like ligands

DNA interaction with scorpiand azamacrocycles has been achieved through modulation of their binding affinities. Studies performed with different experimental techniques provided evidence that pH or metal-driven molecular reorganizations of these ligands r

Scorpiand-like azamacrocycles prevent the chronic establishment of Trypanosoma cruzi in a murine model

Chagas disease is today one of the most important neglected diseases for its upcoming expansion to non-endemic areas and has become a threat to blood recipients in many countries. In this study, the trypanocidal activity of ten derivatives of a family of aza-scorpiand like macrocycles is evaluated against Trypanosoma cruzi in vitro and in vivo murine model in which the acute and chronic phases of Chagas disease were analyzed. The compounds 4, 3 and 1 were found to be more active against the parasite and less toxic against Vero cells than the reference drug benznidazole, 4 being the most active compound, particularly in the chronic phase. While all these compounds showed a remarkable degree of inhibition of the Fe-SOD enzyme of the epimastigote forms of T. cruzi, they produced a negligible inhibition of human CuZn-SOD and Mn-SOD from Escherichia coli. The modifications observed by 1H NMR and the amounts of excreted catabolites by the parasites after treatment suggested that the mechanism of action could be based on interactions of the side chains of the compounds with enzymes of the parasite metabolism. The ultrastructural alterations observed in treated epimastigote forms confirmed that the compounds having the highest activity are those causing the largest cell damage. A complementary histopathological analysis confirmed that the compounds tested were significantly less toxic to mammals than the reference drug.

Synthetic single and double aza-scorpiand macrocycles acting as inhibitors of the antioxidant enzymes iron superoxide dismutase and trypanothione reductase in Trypanosoma cruzi with promising results in a murine model

The anti-chagasic activity of a series of eleven derivatives of aza-scorpiand-like macrocycles, some of them newly synthesised, was assayed. The four compounds with the best selectivity indices in vitro were subjected to in vivo assays. Tests in a murine model of the acute phase of Chagas disease showed a two-fold reduction in parasitaemia compared to that with benznidazole. Furthermore, compounds 7 and 11, with 4-pyridine and phenanthroline substituents in the lateral chain, caused a remarkable decrease in parasitaemia reactivation during the chronic phase after inducing immunosuppression in mice. These activity studies were complemented by measuring their inhibitory effect towards the antioxidant parasite-specific enzymes, iron superoxide dismutase (Fe-SOD) and trypanothione reductase, the metabolites excreted after treatment and ultrastructural alterations. The ability of the selected macrocycles to complex with Fe(ii) and Fe(iii) was studied using potentiometric methods. Detailed molecular dynamics studies provided interesting pointers about the way in which the compounds approach and modify the active centre of Fe-SOD. The activity, low toxicity, stability, low cost of the starting materials and straightforward synthesis make these compounds appropriate molecules for the development of affordable anti-chagasic agents. This journal is

In vitro antileishmanial activity of aza-scorpiand macrocycles. Inhibition of the antioxidant enzyme iron superoxide dismutase

The in vitro leishmanicidal activity of a series of nine aza-scorpiand-like macrocycles, recently synthesized, was tested on Leishmania infantum, Leishmania braziliensis and Leishmania donovani parasites,? using promastigotes and intracellular amastigotes forms. The cytotoxicity of the tested compounds on J774.2 macrophage cells was also measured. Four of the tested compounds (1, 2, 8 and 9) showed selectivity indexes higher than those of the reference drug Glucantime for the three Leishmania species. Moreover, the data on infection rates and on amastigotes showed that compounds 1, 2, 8 and 9 are the most active against the three Leishmania species. The changes in the excretion product profile of parasites treated with the four compounds (1, 2, 8 and 9) were also consistent with substantial cytoplasmic alterations. On the other hand, the most active compounds were potent inhibitors of Fe-SOD in the three parasite species considered, whereas their impact on human CuZn-SOD was low. The high activity, low toxicity, stability, low cost of the starting materials and straightforward synthesis make these compounds appropriate molecules for the development of affordable anti-leishmanicidal agents.

In vitro activity of scorpiand-like azamacrocycle derivatives in promastigotes and intracellular amastigotes of Leishmania infantum and Leishmania braziliensis

The activity of a family scorpiand-like azamacrocycles against Leishmania infantum and Leishmania braziliensis was studied using promastigotes, axenic and intracellular amastigotes forms. All the compounds are more active and less toxic than meglumine ant