213027-19-1

Basic information

• Product Name: 5-[2-(5,5-dimethylhex-1-yn-1-yl)cyclopropyl]-1H-imidazole
• Synonyms: 1H-imidazole, 4-[2-(5,5-dimethyl-1-hexyn-1-yl)cyclopropyl]-; 4-(2-(5,5-dimethylhex-1-ynyl)cyclopropyl)imidazole; 4-[2-(5,5-dimethylhex-1-yn-1-yl)cyclopropyl]-1H-imidazole
• CAS NO: 213027-19-1
• Molecular Formula: C₁₄H₂₀N₂
• Molecular Weight: 216.322
• Mol File: 213027-19-1.mol

Chemical Properties

• Melting Point: 173-175 °C
• Boiling Point: 386.7°C at 760 mmHg
• Flash Point: 188.5°C
• Density: 1.03g/cm³
• Vapor Pressure: 7.72E-06mmHg at 25°C
• Refractive Index: 1.536
• PKA: 14.18±0.10(Predicted)
• CAS DataBase Reference: 5-[2-(5,5-dimethylhex-1-yn-1-yl)cyclopropyl]-1H-imidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-[2-(5,5-dimethylhex-1-yn-1-yl)cyclopropyl]-1H-imidazole(213027-19-1)
• EPA Substance Registry System: 5-[2-(5,5-dimethylhex-1-yn-1-yl)cyclopropyl]-1H-imidazole(213027-19-1)

Safety Data

• Hazardous Substances Data: 213027-19-1(Hazardous Substances Data)

Upstream product

• 223419-91-8 (1R,2R)-4-(2-ethynylcyclopropyl)-1-(triphenylmethyl)imidazole 
• 15672-88-5 neohexyliodide 
• 223419-88-3 4-((1R,2R)-2-(5,5-dimethyl-hex-1-yn-1-yl)-cyclopropyl)-1-trityl-1H-imidazole 

Relevant articles and documents

Preparation of 2-[1H-4(5)-imidazolyl]cyclopropyl derivatives as antagonists of histamine H3 receptor.

The present invention provides compounds having H 3 histamine receptor antagonist activity of the general formula: STR1 R. sub.2 is a hydrogen or a methyl or ethyl group; R 3 is a hydrogen or a methyl or ethyl group;n is 1, 2, 2, 3, 4, 5, or 6; and R 1 is selected from the group consisting of (a) C 3 to C 8 cycloalkyl; (b) phenyl or substituted phenyl; (c) alkyl; (d) heterocyclic; (e) decahydronapthalene; and (f) octahydroindene; with the provisos thatwhen X is H, A can be--CH 2 CH 2--,--COCH 2--,--CONH--,--CON(CH 3), CH= CH,--c≡c--,--CH 2--NH--,--CH. sub.2--N(CH 3)--,--CH(OH)CH. sub.2--,--NH--CH 2--,--N(CH 3)--CH 2--,--CH. sub.2 O--,--CH. sub.2 S--, and--NHCOO--;when X is NH. sub.2, NH(CH. sub.3), N(CH 3) 2, OH, OCH 3, CH 3, SH, and SCH 3 ; A can be--NHCO--,--N(CH 3)--CO--,--NHCH 2--,--N(CH 3)--CH. sub.2--,--CH=CH--;--COCH 2,--CH 2 CH. sub.2--,--CH(OH)CH. sub.2, or--C≡C--; andwhen R. sub.1 and X taken together denote a 5,6 or 6,6 saturated bicyclic ring structure X NH, O, or S and the pharmaceutically acceptable salts, and individual stereoisomers of compounds of structural formula (1.0) above. This invention also provides pharmaceutical compositions comprising a pharmaceutically acceptable carrier in combination with an effective amount of a compound of the above formula and a method of treating conditions in which antagonism of histamine H 3 receptors may be of therapeutic importance.

Design, synthesis, and structure-activity relationships of acetylene- based histamine H3 receptor antagonists

New, potent, and selective histamine H3 receptor antagonists have been synthesized by employing the use of (1) an appropriately positioned nonpolar acetylene spacer group, (2) either a two-carbon straight chain linker or a conformationally restricting trans-cyclopropane ring between the C-4 position of an imidazole headgroup and the acetylene spacer, and (3) a Topliss operational scheme for side-chain substitution for optimizing the hydrophobic domain. Compounds 9-18 are examples synthesized with the two-carbon straight chain linker, whereas 26-31 are analogues prepared by incorporation of the trans-(±)-cyclopropane at the C-4 position of an imidazole headgroup. Synthesis of both the (1R,2R)- and (1S,2S)-cyclopropyl enantiomers of the most potent racemic compound 31 (K(i) = 0.33 ± 0.13 nM) demonstrated a stereopreference in H3 receptor binding affinity for the (1R,2R) enantiomer 32 (K(i) = 0.18 ± 0.04 nM) versus the (1S,2S) enantiomer 33 (K(i) = 5.3 ± 0.5 nM). (1R,2R)-4-(2-(5,5-Dimethylhex-1-ynyl)cyclopropyl)-imidazole (32) is one of the most potent histamine H3 receptor antagonists reported to date.