38838-27-6

Basic information

• Product Name: N-(3-hydroxy-2-iodo-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c][7]annulen-5-yl)acetamide
• CAS NO: 38838-27-6
• Molecular Formula: C₂₀H₂₂INO₅
• Molecular Weight: 483.2969
• Mol File: 38838-27-6.mol

Chemical Properties

• Boiling Point: 615.8°C at 760 mmHg
• Flash Point: 326.2°C
• Density: 1.61g/cm³
• Vapor Pressure: 9.36E-16mmHg at 25°C
• Refractive Index: 1.653
• CAS DataBase Reference: N-(3-hydroxy-2-iodo-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c][7]annulen-5-yl)acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(3-hydroxy-2-iodo-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c][7]annulen-5-yl)acetamide(38838-27-6)
• EPA Substance Registry System: N-(3-hydroxy-2-iodo-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c][7]annulen-5-yl)acetamide(38838-27-6)

Safety Data

• Hazardous Substances Data: 38838-27-6(Hazardous Substances Data)

Usage

Uses

As the specific applications of N-(3-hydroxy-2-iodo-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c][7]annulen-5-yl)acetamide are not provided in the materials, it is not possible to list its uses based on the information given. However, given the presence of pharmacologically relevant functional groups, it can be hypothesized that N-(3-hydroxy-2-iodo-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c][7]annulen-5-yl)acetamide may have potential applications in various fields such as pharmaceuticals, materials science, or chemical research. Further investigation would be necessary to confirm its practical uses and benefits in these or other industries.

Upstream product

• 477-27-0 colchiceine 
• 64-86-8 colchicine 

Relevant articles and documents

Allocolchicinoids bearing a Michael acceptor fragment for possible irreversible binding of tubulin

We describe an attempt to apply the concept of covalent binding towards the highly active allocolchicinoids selected on the basis of SAR analysis of previously synthesized molecules. To achieve the irreversible binding of the agent to the cysteine residues of the colchicine site of tubulin protein, we synthesized a number of new allocolchicinoids bearing the acceptor moiety. Some of the new derivatives possess cytotoxic activity against COLO-357, BxPC-3, HaCaT, and HEK293 cell lines in a low nanomolar range of concentrations. A substoichiometric mode of microtubule assembly inhibition was demonstrated. The most active compounds possess close to colchicine general toxicity on mice. This journal is

Synthesis of Bifunctional Furano-Allocolchicinoids

An efficient seven-step semisynthetic approach towards non-racemic bifunctional furano-allocolchicinoids, starting from naturally occurring colchicine is presented. The Pd-catalyzed domino Sonogashira coupling/5- endo - dig cyclization was employed as the key step. The prepared compounds exhibited substantial cytotoxicity against T3M4, MiaPaCa-2, Colo-357, and PANC-1 cell lines. The presence of two functionalities with different reactivity (hydroxyl and amino groups) in the target molecules allows for an easy conjugation of furano-allocolchicinoids with drug delivery carriers, and opens promising opportunities for their further exploitation in the search of therapeutics..

Discovery of dihydrofuranoallocolchicinoids - Highly potent antimitotic agents with low acute toxicity

Two series of heterocyclic colchicinoids bearing β-methylenedihydrofuran or 2H-pyran-2-one fragments were synthesized by the intramolecular Heck reaction. Methylenedihydrofuran compounds 9a and 9h were found to be the most cytotoxic among currently known

Phospholipidic Colchicinoids as Promising Prodrugs Incorporated into Enzyme-Responsive Liposomes: Chemical, Biophysical, and Enzymological Aspects

Enzyme-responsive liposomes release their cargo in response to pathologically increased levels of enzymes at the target site. We report herein an assembly of phospholipase A2-responsive liposomes based on colchicinoid lipid prodrugs incorporated into lipid bilayer of the nanosized vesicles. The liposomes were constructed to addresses two important issues: (i) the lipid prodrugs were designed to fit the structure of the enzyme binding site; and (ii) the concept of lateral pressure profile was used to design lipid prodrugs that introduce almost no distortions into the lipid bilayer packing, thus ensuring that corresponding liposomes are stable. The colchicinoid agents exhibit antiproliferative activity in subnanomolar range of concentrations.

A Facile Synthetic Approach to Nonracemic Substituted Pyrrolo-allocolchicinoids Starting from Natural Colchicine

A six-step semisynthetic approach towards chiral nonracemic pyrrolo-allocolchicinoids starting from naturally occurring colchicine was developed. The synthetic scheme includes an electrocyclic tropolone ring contraction to afford allocolchicinic acid followed by the Curtius reaction, giving the corresponding aniline. The Sandmeyer reaction and copper-mediated hydrazination gave hydrazine-substituted allocolchicine. This was introduced into the Fischer indole synthesis, affording libraries of regioisomeric indole-based allocolchicine congeners.

Gold-catalyzed cyclization in the synthesis of antimitotic 2,3-dihydrobenzo[b]oxepine derivatives of colchicine

New allocolchicine derivatives bearing 2,3-dihydrobenzo[b]oxepine moiety were synthesized via gold-catalyzed cyclization as a key synthetic step. The obtained 2,3-dihydrobenzo[b]oxepine-containing allocolchicinoids possess cytotoxic activity against HEK293, PANC-1, COL0357, HeLa, and Colon26 cancer cell lines at low micromolar range of concentrations.

Synthesis and cytostatic properties of polyfunctionalized furanoallocolchicinoids

A series of furan-based allocolchicinoids was prepared from commercially available colchicine via a nine-step reaction sequence. Cytostatic activity, cell cycle arrest, apoptosis, tubulin and F-actin expression were studied in vitro in 2D and 3D cultures of normal and tumor epithelial keratinocytes, endothelial and mesenchymal cells. Among the prepared furanoallocolchicine analogues, 14a and 7a displayed the most pronounced anti-cancer activity. These compounds induced two types of effects: (a) cell cycle arrest in the G2/M phase as a direct consequence of effective tubulin binding (metaphase effect), and (b) pronounced cell stress (as evidenced by the overexpression of tubulin and F-actin), which was caused by the hyperpolarization of mitochondrial and lysosomal membranes (interphase effect).

Synthesis of new sulfur-containing derivatives of furanoallocolchicinoids

Reaction of hydroxyl-containing heterocyclic colchicinoids with S-nucleophiles led to the formation of furanoallocolchicinoid sulfides in a high yield.

Synthesis and biological evaluation of furanoallocolchicinoids

A series of conformationally flexible furan-derived allocolchicinoids was prepared from commercially available colchicine in good to excellent yields using a three-step reaction sequence. Cytotoxicity studies indicated the potent activity of two compounds against human epithelial and lymphoid cell lines (AsPC-1, HEK293, and Jurkat) as well as against Wnt-1 related murine epithelial cell line W1308. The results of in vitro experiments demonstrated that the major effect of these compounds was the induction of cell cycle arrest in the G2/M phase as a direct consequence of effective tubulin binding. In vivo testing of the most potent furanoallocolchicinoid 10c using C57BL/6 mice inoculated with Wnt-1 tumor cells indicated significant inhibition of the tumor growth.

A convenient entry to new C-7-modified colchicinoids through azide alkyne [3+2] cycloaddition: Application of ring-contractive rearrangements

Reliable procedures for the preparation of azides derived from colchicine (1), allocolchicine (3) and N-acetylcolchinol (4a) were developed. These azides were then employed in Cu-catalyzed Huisgen-Sharpless [3+2] cycloaddition ("click") reactions with alkynes under microwave irradiation. The method developed opens a convenient and efficient access to libraries of new C-7-modified colchicinoids (triazole derivatives). In addition, a plausible mechanistic rationale for the colchicine-allocolchicine rearrangement is suggested. The Japan Institute of Heterocyclic Chemistry.