70209-83-5

Usage

Cyclopropane derivative

The compound is based on a cyclopropane ring, which is a three-carbon ring with bond angles of 60 degrees, making it a strained and highly reactive structure.

Phenyl group attachment

A phenyl group (a six-carbon ring with a delocalized electron system) is attached to the cyclopropane ring, contributing to the compound's stability and potential biological activity.

Carboxylic acid group

The compound contains a carboxylic acid group (-COOH), which is a functional group known for its acidic properties and ability to form hydrogen bonds, making it important in medicinal chemistry and drug development.

Hydroxymethyl group attachment

A hydroxymethyl group (-CH2OH) is also attached to the cyclopropane ring, adding an additional hydrophilic character to the molecule and potentially affecting its biological activity and solubility.

Potential applications in medicinal chemistry

Due to its unique structure and potential biological activity, 2-(hydroxymethyl)-1-phenylcyclopropanecarboxylic acid may be used in the development of new drugs and therapeutic agents.

Building block in organic synthesis

The compound can be used as a starting material or intermediate in the preparation of other chemical compounds, allowing for the synthesis of a diverse range of molecules with various applications.

Upstream product

• 63106-93-4 (1S,5R)-1-phenyl-3-oxabicyclo[3.1.0]hexan-2-one 
• 51594-55-9 (R)-(-)-epichlorohydrin 
• 140-29-4 phenylacetonitrile 
• 67843-74-7 (S)-epichlorohydrin 

Downstream Products

• 175131-61-0 C₁₅H₂₂N₂O*ClH 
• 1237261-65-2 (1S,2R)-2-((1,3-dioxoisoindolin-2-yl)methyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide-cyclopropanecarboxamide 
• 63106-93-4 (1S,5R)-1-phenyl-3-oxabicyclo[3.1.0]hexan-2-one 
• 101152-94-7 (1S,2R)-milnacipran hydrochloride 

Relevant academic research and scientific papers

Preparation method of levomilnacipran diastereoisomer

The invention provides a preparation method of a levomilnacipran diastereoisomer. The preparation method comprises the following steps: taking benzyl cyanide and R-epichlorohydrin or S-epichlorohydrinas starting materials, performing cycloalkylation on th

(+)-Methyl (1 R, 2S)-2-{[4-(4-Chlorophenyl)-4-hydroxypiperidin-1-yl]methyl}-1-phenylcyclopropanecarboxylate [(+)-MR200] derivatives as potent and selective sigma receptor ligands: Stereochemistry and pharmacological properties

Methoxycarbonyl-1-phenyl-2-cyclopropylmethyl based derivatives cis-(+)-1a [cis-(+)-MR200], cis-(-)-1a [cis-(-)-MR201], and trans-(±)-1a [trans-(±)-MR204], have been identified as new potent sigma (σ) receptor ligands. In the present paper, novel enantiomerically pure analogues were synthesized and optimized for their σ receptor affinity and selectivity. Docking studies rationalized the results obtained in the radioligand binding assay. Absolute stereochemistry was unequivocally established by X-ray analysis of precursor trans-(+)-5a as camphorsulfonyl derivative 9. The most promising compound, trans-(+)-1d, showed remarkable selectivity over a panel of more than 15 receptors as well as good chemical and enzymatic stability in human plasma. An in vivo evaluation evidenced that trans-(+)-1d, in contrast to trans-(-)-1d, cis-(+)-1d, or cis-(-)-1d, which behave as σ1 antagonists, exhibited a σ1 agonist profile. These data clearly demonstrated that compound trans-(+)-1d, due to its σ1 agonist activity and favorable receptor selectivity and stability, provided an useful tool for the study of σ1 receptors.

PROCESS FOR THE PREPARATION OF (1S,2R)-MILNACIPRAN

The invention relates to a process for the preparation of Levomilnacipran, a compound useful in the treatment of depression, comprising the following steps: a) directly converting the enantiomerically enriched form of alcohol (D) into the enantiomerically enriched form of the phthalimido derivative (C) by treatment with phthalimide in the presence of a trialkyl or triarylphosphine and of a dialkyl azodicarboxylate, formula (I) wherein the amount of phthalimide is comprised between 1 and 1.3 equivalents with respect to the molar amount of alcohol (D) used, and the amounts of both the phosphine and the azodicarboxylate are comprised, independently from each other, between 1 and 1.5 equivalents with respect to the molar amount of alcohol (D) used; b) deblocking the enantiomerically enriched form of the phthalimido derivative (C) to obtain Levomilnacipran, formula (II).

Conformational restriction approach to β-Secretase (BACE1) inhibitors: Effect of a cyclopropane ring to induce an alternative binding mode

Improvement of a drugs binding activity using the conformational restriction approach with sp3 hybridized carbon is becoming a key strategy in drug discovery. We applied this approach to BACE1 inhibitors and designed four stereoisomeric cyclopropane compounds in which the ethylene linker of a known amidine-type inhibitor 2 was replaced with chiral cyclopropane rings. The synthesis and biologic evaluation of these compounds revealed that the cis-(1S,2R) isomer 6 exhibited the most potent BACE1 inhibitory activity among them. X-ray structure analysis of the complex of 6 and BACE1 revealed that its unique binding mode is due to the apparent CH-π interaction between the rigid cyclopropane ring and the Tyr71 side chain. A derivatization study using 6 as a lead molecule led to the development of highly potent inhibitors in which the structure-activity relationship as well as the binding mode of the compounds clearly differ from those of known amidine-type inhibitors.