851916-02-4

Basic information

• Product Name: benzene-1,4-bis[aminomethylidene(bisphosphonic)] acid
• Synonyms: benzene-1,4-bis[aminomethylidene(bisphosphonic)] acid
• CAS NO: 851916-02-4
• Molecular Weight: 456.116
• Mol File: 851916-02-4.mol

Chemical Properties

• CAS DataBase Reference: benzene-1,4-bis[aminomethylidene(bisphosphonic)] acid(CAS DataBase Reference)
• NIST Chemistry Reference: benzene-1,4-bis[aminomethylidene(bisphosphonic)] acid(851916-02-4)
• EPA Substance Registry System: benzene-1,4-bis[aminomethylidene(bisphosphonic)] acid(851916-02-4)

Safety Data

• Hazardous Substances Data: 851916-02-4(Hazardous Substances Data)

Upstream product

• 935-16-0 1,4-phenylenediisocyanide 
• 6262-22-2 N-(4-formylaminophenyl)formamide 
• 106-50-3 1,4-phenylenediamine 
• 1620164-64-8 octaethyl benzene-1,4-bis[aminomethylidene(bisphosphonate)] 

Relevant articles and documents

Biological effects of aromatic bis[aminomethylidenebis(phosphonic)] acids in osteoclast precursors in vitro

Nitrogen-containing bisphosphonates (N-BPs) inhibit bone resorption by preventing osteoclast activity. Most clinically used BPs are hydroxybisphosphonates with the exception of incadronate, which belongs to the class of aminomethylidenebisphosphonic acids

Three-component reaction of diamines with triethyl orthoformate and diethyl phosphite and anti-proliferative and antiosteoporotic activities of the products

A three-component reaction between diamines (diaminobenzenes, diaminocyclohexanes, and piperazines), triethyl orthoformate, and diethyl phosphite was studied in some detail. In the case of 1,3- and 1,4-diamines and piperazines, products of the substitution of two amino moieties—the corresponding tetraphosphonic acids—were obtained. In the cases of 1,2-diaminobenzene, 1,2-diaminocyclohexanes and 1,2-diaminocyclohexenes, only one amino group reacted. This is most likely the result of the formation of hydrogen bonding between the phosphonate oxygen and a hydrogen of the adjacent amino group, which caused a decrease in the reactivity of the amino group. Most of the obtained compounds inhibited the proliferation of RAW 264.7 macrophages, PC-3 human prostate cancer cells, and MCF-7 human breast cancer cells, with 1, trans-7, and 16 showing broad nonspecific activity, which makes these compounds especially interesting in the context of anti-osteolytic treatment and the blocking of interactions and mutual activation of osteoclasts and tumor metastatic cells. These compounds exhibit similar activity to zoledronic acid and higher activity than incadronic acid, which were used as controls. However, studies of sheep with induced osteoporosis carried out with compound trans-7 did not support this assumption.

Synthesis and antiproliferative activity of aromatic and aliphatic bis[aminomethylidene(bisphosphonic)] acids

A series of aromatic and aliphatic bis[aminomethylidene(bisphosphonic)] acids was synthesized in the reaction of triethylphosphite with isonitriles followed by hydrolysis or dealkylation. The in vitro anti-proliferative effect of all synthesized tetraphosphonic acids against MCF-7 breast cancer cells, J774E macrophages and HL-60 promyelocytic leukemia cells was determined. Three aromatic derivatives (5a, 5f and 5j) showed a similar or higher anti-proliferative activity than zoledronic acid.