1455460-32-8

Basic information

• Product Name: C₃₇H₅₅ClO₅
• CAS NO: 1455460-32-8
• Molecular Weight: 615.294
• Mol File: 1455460-32-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: C₃₇H₅₅ClO₅(CAS DataBase Reference)
• NIST Chemistry Reference: C₃₇H₅₅ClO₅(1455460-32-8)
• EPA Substance Registry System: C₃₇H₅₅ClO₅(1455460-32-8)

Safety Data

• Hazardous Substances Data: 1455460-32-8(Hazardous Substances Data)

Upstream product

• 78518-73-7 sipholenol-A 
• 790-41-0 4-chlorobenzoic anhydride 

Relevant articles and documents

Optimization of Marine Triterpene Sipholenols as Inhibitors of Breast Cancer Migration and Invasion

SipholenolA, a sipholane triterpene isolated from the Red Sea sponge Callyspongia siphonella, has the ability to reverse multidrug resistance in cancer cells that overexpress P-glycoprotein (P-gp). Here, the antimigratory activity of sipholenolA and analogues are reported against the highly metastatic human breast cancer cell line MDA-MB-231 in a wound-healing assay. SipholenolA and sipholenoneA were semisynthetically optimized using ligand-based strategies to generate structurally diverse analogues in an attempt to maximize their antimigratory activity. A total of 22 semisynthetic ester, ether, oxime, and carbamate analogues were generated and identified by extensive one- and two-dimensional NMR spectroscopy and high-resolution mass spectrometry analyses. SipholenolA 4β-4-chlorobenzoate and 19,20-anhydrosipholenolA 4β-4-chlorobenzoate esters were the most potent of all tested analogues in the wound-healing assay, with IC50 values of 5.3 and 5.9μM, respectively. Generally, ester derivatives showed better antimigratory activities than the carbamate analogues. A KINOMEscan of 19,20-anhydrosipholenolA 4β-benzoate ester against 451 human protein kinases identified protein tyrosine kinase6 (PTK6) as a potential target. In breast tumor cells, PTK6 promotes growth factor signaling and migration, and as such the semisynthetic sipholanes were evaluated for their ability to inhibit PTK6 phosphorylation in vitro. The two analogues with the highest antimigratory activities, sipholenolA 4β-4-chlorobenzoate and 19,20-anhydrosipholenolA 4β-4-chlorobenzoate esters, also exhibited the most potent inhibition of PTK6 phosphorylation inhibition. None of the compounds exhibited cytotoxicity in a normal epithelial breast cell line. These derivatives were evaluated in an invitro invasion assay, where sipholenolA succinate potently inhibited MDA-MB-231 cell invasion at 10μM. These results highlight sipholane triterpenoids as novel antimigratory marine natural products with potential for further development as agents for the control of metastatic breast malignancies.