124351-91-3

Basic information

• Product Name: [(cyclopropylamino)methanediyl]bis(phosphonic acid)
• CAS NO: 124351-91-3
• Molecular Formula: C₄H₁₁NO₆P₂
• Molecular Weight: 231.0808
• Mol File: 124351-91-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 570.6°C at 760 mmHg
• Flash Point: 298.9°C
• Density: 1.8g/cm³
• Vapor Pressure: 1.64E-14mmHg at 25°C
• Refractive Index: 1.566
• CAS DataBase Reference: [(cyclopropylamino)methanediyl]bis(phosphonic acid)(CAS DataBase Reference)
• NIST Chemistry Reference: [(cyclopropylamino)methanediyl]bis(phosphonic acid)(124351-91-3)
• EPA Substance Registry System: [(cyclopropylamino)methanediyl]bis(phosphonic acid)(124351-91-3)

Safety Data

• Hazardous Substances Data: 124351-91-3(Hazardous Substances Data)

Relevant articles and documents

Bisphosphonate inhibitors of squalene synthase protect cells against cholesterol-dependent cytolysins

Certain species of pathogenic bacteria damage tissues by secreting cholesterol-dependent cytolysins, which form pores in the plasma membranes of animal cells. However, reducing cholesterol protects cells against these cytolysins. As the first committed st

3-D QSAR Investigations of the Inhibition of Leishmania major Farnesyl Pyrophosphate Synthase by Bisphosphonates

We report the activities of 62 bisphosphonatesas inhibitors of the Leishmania major mevalonate/isoprene biosynthesis pathway enzyme, farnesyl pyrophosphate synthase. The compounds investigated exhibit activities (IC 50 values) ranging from ～100 nM to ～80 μM (corresponding to Ki values as low as 10 nM). The most active compounds were found to be zoledronate (whose single-crystal X-ray structure is reported), pyridinyl-ethane-1-hydroxy-1,1-bisphosphonates or picolyl aminomethylene bisphosphonates. However, N-alicyclic amino-methylene bisphosphonates, such as incadronate (N-cycloheptyl aminomethylene bisphosphonate), as well as aliphatic aminomethylene bisphosphonates containing short (n = 4, 5) alkyl chains, were also active, with 1C50 values in the 200-1700 nM range (corresponding to Ki values of ～20-170 nM). Bisphosphonates containing longer or multiple (N,N-) alkyl substitutions were inactive, as were aromatic species lacking an o- or m-nitrogen atom in the ring, or possessing multiple halogen substitutions or a p-amino group. To put these observations on a more quantitative structural basis, we used three-dimensional quantitative structure-activity relationship techniques: comparative molecular field analysis (CoMFA) and comparative molecular similarity index analysis (CoMSIA), to investigate which structural features correlated with high activity. Training set results (N = 62 compounds) yielded good correlations with each technique (R2 = 0.87 and 0.88, respectively), and were further validated by using a training/test set approach. Test set results (N = 24 compounds) indicated that IC50 values could be predicted within factors of 2.9 and 2.7 for the CoMFA and CoMSIA methods, respectively. The CoMSIA fields indicated that a positive charge in the bisphosphonate side chain and a hydrophobic feature contributed significantly to activity. Overall, these results are of general interest since they represent the first detailed quantitative structure-activity relationship study of the inhibition of an expressed farnesyl pyrophosphate synthase enzyme by bisphosphonate inhibitors and that the activity of these inhibitors can be predicted within about a factor of 3 by using 3D-QSAR techniques.

(Cycloalkylamino)methylenebis(phosphonic acid)

(Cycloalkylamino)methylenebis(phosphonic acid) represented by the general formula: STR1 in which, R, R1, R2, R3 and R4 represent a hydrogen atom or a lower alkyl group, and n represents an integer from 3 to 10, a lower alkyl ester thereof or a pharmaceutically acceptable salt thereof; and a bone-resorption inhibitor and an anti-arthritis containing the same.