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Mal-C2-cyclohexylcarboxyl-hydrazide hydrochloride

Mal-C2-cyclohexylcarboxyl-hydrazide hydrochloride

Name: Mal-C2-cyclohexylcarboxyl-hydrazide hydrochloride
Brand: BOC Sciences
Rating: 5 (1 reviews)

CAS No.: 174422-72-1

Cat No.: BP-500616 4.5

Mal-C2-cyclohexylcarboxyl-hydrazide hydrochloride is a bifunctional PROTAC linker building block featuring a maleimide-derived electrophile for thiol–maleimide conjugation and a hydrazide handle for subsequent coupling to carbonyl- or activated-carboxylate-containing partners. The C2 spacer and cyclohexylcarboxyl hydrazide motif provide a defined, relatively rigid yet flexible linkage environment that can tune the effective distance and orientation between the warhead-binding element and the E3 ligase-recruiting moiety. In PROTAC workflows, the maleimide group enables rapid, chemoselective attachment to cysteine residues on engineered proteins or to thiol-bearing ligands, while the hydrazide functionality supports orthogonal derivatization to generate stable conjugates. This reagent is valuable for constructing targeted protein degradation probes where controlled linker length and conjugation chemistry are critical for achieving productive ternary complex formation and optimizing degradation potency and selectivity in cell-based assays.

Structure of 174422-72-1

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Molecular Formula

C₁₂H₁₈ClN₃O₃

Molecular Weight

287.74

* For research and manufacturing use only. Not for human or clinical use.

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Solubility

In H2O: 33.33 mg/mL (115.83 mM; Need ultrasonic)<br/>In DMSO: 16.67 mg/mL (57.93 mM; Need ultrasonic)

Storage

Powder, -20°C, 3 years; 4°C, 2 years; In solvent, -80°C, 6 months; -20°C, 1 month

Shipping

Room temperature in continental US; may vary elsewhere.

IUPACName

4-[(2,5-dioxopyrrol-1-yl)methyl]cyclohexane-1-carbohydrazide;hydrochloride

InChI Key

CKGAFBJFAXITJV-UHFFFAOYSA-N

InChI

InChI=1S/C12H17N3O3.ClH/c13-14-12(18)9-3-1-8(2-4-9)7-15-10(16)5-6-11(15)17;/h5-6,8-9H,1-4,7,13H2,(H,14,18);1H

SMILES

C1CC(CCC1CN2C(=O)C=CC2=O)C(=O)NN.Cl

1. Metal-free and regiospecific synthesis of 3-arylindoles

Chuangchuang Xu, Wenlai Xie, Jiaxi Xu Org Biomol Chem. 2020 Apr 8;18(14):2661-2671.doi: 10.1039/d0ob00317d.

A convenient, metal-free, and organic acid-base promoted synthetic method to prepare 3-arylindoles from 3-aryloxirane-2-carbonitriles and arylhydrazine hydrochlorides has been developed. In the reaction, the organic acid catalyzes a tandem nucleophilic ring-opening reaction of aryloxiranecarbonitriles and arylhydrazine hydrochlorides and Fischer indolization. The organic base triethylamine plays a crucial role in the final elimination step in the Fischer indole synthesis, affording 3-arylindoles regiospecifically. The reaction features advantages of microwave acceleration, non-metal participation, short reaction time, organic acid-base co-catalysis, and broad substrate scope.

2. 1-Haloacylpiperazines

S Groszkowski, J Sienkiewicz, L Korzycka Pol J Pharmacol Pharm. 1975 Apr-Jun;27(2):183-6.

By direct acylation of piperazine with halogenocarboxylic acid chlorides in acid medium, the hydrochlorides of 1-haloacylpiperazines were obtained.

3. Diastereo- and enantioselective anti-selective hydrogenation of α-amino-β-keto ester hydrochlorides and related compounds using transition-metal-chiral-bisphosphine catalysts

Yasumasa Hamada Chem Rec. 2014 Apr;14(2):235-50.doi: 10.1002/tcr.201300032.Epub 2014 Feb 18.

This review describes our recent works on the diastereo- and enantioselective synthesis of anti-β-hydroxy-α-amino acid esters using transition-metal-chiral-bisphosphine catalysts. A variety of transition metals, namely ruthenium (Ru), rhodium (Rh), iridium (Ir), and nickel (Ni), in combination with chiral bisphosphines, worked well as catalysts for the direct anti-selective asymmetric hydrogenation of α-amino-β-keto ester hydrochlorides, yielding anti-β-hydroxy-α-amino acid esters via dynamic kinetic resolution (DKR) in excellent yields and diastereo- and enantioselectivities. The Ru-catalyzed asymmetric hydrogenation of α-amino-β-ketoesters via DKR is the first example of generating anti-β-hydroxy-α-amino acids. Complexes of iridium and axially chiral bisphosphines catalyze an efficient asymmetric hydrogenation of α-amino-β-keto ester hydrochlorides via dynamic kinetic resolution. A homogeneous Ni-chiral-bisphosphine complex also catalyzes an efficient asymmetric hydrogenation of α-amino-β-keto ester hydrochlorides in an anti-selective manner. As a related process, the asymmetric hydrogenation of the configurationally stable substituted α-aminoketones using a Ni catalyst via DKR is also described.

ConcentrationVolumeMass	1 mg	5 mg	10 mg
1 mM	3.4754 mL	17.3768 mL	34.7536 mL
5 mM	0.6951 mL	3.4754 mL	6.9507 mL
10 mM	0.3475 mL	1.7377 mL	3.4754 mL

Mal-C2-cyclohexylcarboxyl-hydrazide hydrochloride, provides a chemically robust hydrazide handle suitable for constructing bifunctional degraders. Its functional-group pattern supports reliable conjugation strategies that connect target-binding ligands to E3 ligase recruiters while maintaining appropriate linker flexibility and polarity. Researchers commonly use hydrazide-bearing linkers to enable controlled amide/semicarbazide-type coupling workflows, supporting systematic optimization of ternary-complex formation and targeted protein degradation.

Structure: The molecule contains a hydrazide core, a cyclohexylcarboxyl-derived acyl fragment, and a malonyl-type C2 spacer motif. It features multiple hydrogen-bonding sites from the hydrazide and amide functionalities, with amide and hydrazone-relevant connectivity enabling stable conjugates. The hydrochloride salt form improves handling and aqueous compatibility.

Reactivity: Hydrazide linkers are typically employed in PROTAC synthesis via acyl activation and subsequent amide-forming coupling, or through hydrazide/activated ester condensation steps to install the linker onto ligand fragments. Suitable conditions often involve mild base or coupling reagents, with polar aprotic solvents such as DMF or DMSO to promote activation while limiting side reactions. Reaction monitoring by LC-MS or NMR is recommended to confirm complete conversion and preserve functional-group integrity.

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* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C₁V₁ = C₂V₂