707-16-4

Usage

Uses

Used in Pharmaceutical Industry:
NSC22850 is used as an anticancer agent for its ability to induce DNA damage and apoptosis in cancer cells, making it a potential treatment for various types of cancer.
NSC22850 is used as a research compound for studying the mechanisms of topoisomerase I inhibition and its role in cancer cell death, contributing to the advancement of cancer therapeutics.
NSC22850 is used in drug development for the creation of novel cancer-fighting drugs, given its improved water solubility and therapeutic efficacy, which may enhance the effectiveness and safety of cancer treatments.

InChI:InChI=1/C9H14N2O2/c12-7-9(11-8(13)10-7)5-3-1-2-4-6-9/h1-6H2,(H2,10,11,12,13)

Upstream product

• 151-50-8 potassium cyanide 
• 502-42-1 cycloheptanone 
• 143-33-9 sodium cyanide 
• 506-87-6 ammonium carbonate 
• 773837-37-9 sodium cyanide 

Downstream Products

• 734-04-3 5,5-Hexamethylen-3-morpholinomethyl-hydantoin 
• 6949-77-5 1-aminocycloheptane-1-carboxylic acid 
• 106663-29-0 3-(3-Phenyl-propyl)-1,3-diaza-spiro[4.6]undecane-2,4-dione 
• 197794-44-8 1-Benzyloxycarbonylamino-cycloheptanecarboxylic acid 
• 92398-64-6 N-(benzyloxycarbonyl)-β-benzyl-L-aspartyl-α-aminocycloheptanecarboxylic acid methyl ester 
• 106663-45-0 4-Hydroxy-3-(3-phenyl-propyl)-1,3-diaza-spiro[4.6]undecan-2-one 
• 199330-56-8 1-(tert-butoxycarbonylamino) cycloheptanecarboxylic acid 
• 92398-50-0 methyl 1-amino-cycloheptanecarboxylate hydrochloride 

Relevant academic research and scientific papers

Synthesis, structural characterization, DFT calculations and antiproliferative evaluation of novel spirohydantoin derivatives containing a substituted benzyl moiety

Two series of cycloalkanespiro-5-hydantoins, namely cyclohexanespiro-5-hydantoins and cycloheptanespiro-5-hydantoins with a 4-substituted benzyl or a 2-(4-substituted phenyl)-2-oxoethyl group at N3 position, were synthesized and their effects on proliferation of human colon (HCT-116), leukemia (K562) and breast (MDA-MB-231) cancer cell lines were tested. For comparison, we also described the 5,5-diphenylhydantoin analogues. The structural features of the investigated compounds were characterized by elemental analysis, FT-IR, UV–Vis, 1H and 13C NMR spectroscopy and X-ray crystallography. Regarding their structure–activity relationships, it was shown that the substitution on the benzyl moiety with the methoxy, chloro or bromo group potentiated the antiproliferative activity relative to the parent compounds, while an increase in the size of the cycloalkyl group resulted mostly in a decrease of the antiproliferative activity. The single crystal X-ray analysis revealed the existence of dimers and chains formed by the N–H?O hydrogen bonds. The analysis of the molecular descriptors of Lipinski demonstrated that all investigated compounds obeyed the rule of five. To further understand their geometry and electronic structure, DFT calculations with B3LYP method using 6-311++G(d,p) basic set were performed. In this context, the UV–Vis spectra of the investigated compounds were analyzed in detail, whereby the predicted absorption spectra from DFT calculation matched the experimentally obtained ones, with a good correlation. The interesting physico-chemical and pharmacologically relevant properties of the investigated compounds warrant their further investigation.

Towards understanding intermolecular interactions in hydantoin derivatives: the case of cycloalkane-5-spirohydantoins tethered with a halogenated benzyl moiety

A series of cycloalkane-5-spirohydantoins bearing a halogeno substituted benzyl group (X = Cl and Br) in position 3 has been synthesized and their structures (1-6) have been determined by a single crystal X-ray diffraction method. These compounds have multiple functional groups, which allow greater competition and/or cooperation among the different intermolecular interactions in the formation of their crystal structures. The molecules are linked together by paired N-H?O hydrogen bonds in R22(8) rings, while the C-H?O interactions lead to their further association into double chains. The contribution of the cycloalkyl ring depends on its conformational flexibility and the multiple C-H donor implications. In the case of compounds 1-4 bearing the cyclopentyl or the cyclohexyl ring, halogen bonding (X?O) interactions give rise to a supramolecular pseudo-hexagonal network. In addition, the C-H?X interactions with a higher degree of multifurcation at the halogen acceptor have an important role in the formation of the crystal structure. Regarding compounds 5 and 6 with the cycloheptane ring, the X?O interaction is absent, and along with the C-H?X interactions, these compounds realize an alternative crystal structure with an emphasis on the X?π interactions. The lattice energies of all these crystal structures, as well as the intermolecular pair energies, have been calculated using PIXEL and further partitioned into coulombic, dispersive, polarization and repulsive factors. The crystal structures have also been subjected to Hirshfeld surface analysis which reveals that approximately 75% of the close contacts correspond to relatively weak interactions. The application of both concepts has provided a new insight into the relationship between the molecular interactions and crystal structures of the hydantoin derivatives.

Microwave-assisted synthesis of cycloalkanespirohydantoins and piperidinespirohydantoins as precursors of restricted α-amino acids

Cycloalkanespirohydantoins 3 and piperidinespirohydantoins 4 were synthesized from cycloalkanones 9 and piperidones 10 under microwave-assisted conditions. Results are compared with those obtained under thermal conditions. Cycloalkanespirohydantoins 3 were N-protected with Boc group and hydrolyzed under basic conditions to obtain five, six and seven-membered ring restricted α-amino acids 12 in very good overall yields (76-94%). ARKAT USA, Inc.

Synthesis and characterization of novel cycloalkanespiro-5-hydantoin phosphonic acids

A series of new cycloalkanespiro-5-hydantoin phosphonic acids have been synthesized and characterized. The mixture of [(2,4-dioxo-1,3-diazaspiro-alkane- 3-yl)-methyl]phosphonic acids and [(2,4-dioxo-1,3-diazaspiro-alkane-1,3-diyl) dimethyl]diphospho-nic acids was obtained from cycloalkanespiro-5-hydantoins, formaldehyde, and phosphorus trichloride in a molar ratio of 1:2:2, by a procedure modified by us. Their structures were proved by means of IR, 1H, 13C{1H} and 31P NMR spectroscopy. Copyright Taylor & Francis Group, LLC.

Novel N-(phosphonomethyl) glycine derivatives: Design, characterization and biological activity

A series of Cα,α-disubstituted cyclic derivatives of N-(phosphonomethyl) glycine have been synthesized and characterized. They exhibited moderate clastogenicity, low antiproliferative activity on mice bone marrow cells and well expressed cytotoxicity against human tumor cell lines. The 8- and 12-membered cyclic analogs proved superior to the remaining compounds and were found to trigger apoptotic cell death in DOHH-2 cells. The latter compound caused 50% inhibition of the viability of hemobastose-derived cell lines at concentrations ranging from 20 to 67 μM.

Aminoderivatives of cycloalkanespirohydantoins: Synthesis and biological activity

3-Aminocycloalkanespiro-5-hydantoins were synthesized and their biological activity was studied. In contrast to hydantoins, these compounds failed to induce either anticonvulsive effects in the central nervous system or inhibitory effects on cholinergic contractions in the enteric nervous system. However, they exerted well pronounced, atropinsensitive, contractile effects on the guinea-pig ileum longitudinal muscle preparations. Structure-activity relationships established allow the assumption that: (i) the reduction of the ring size in the molecule of the spirohydantoins leads to an increase in the potency of the respective analogue to induce contractile effect; (ii) the introduction of -NH2 in position 3 increases the ability of all the compounds studied to exert contractions; (iii) the enlargement of the ring leads to: (1) an increase of the degree of desensitization of the preparations; and (2) a decrease (except 1a) of the potency of the analogues to exert contractile effects.

Hydrogen-bonded tapes based on symmetrically substituted diketopiperazines: A robust structural motif for the engineering of molecular solids

A series of eight symmetrically substituted diketopiperazines (DKPs) derived from 1-amino-1-carboxycycloalkanes (n = 3-7; 3,3,5,5-tetramethylcyclohexane; 4,4-dimethylcyclohexane; 2-indan) were synthesized and their crystal structures determined. In the solid state, all eight compounds form two pairs of hydrogen bonds with two adjacent molecules to form a one-dimensional structure that we refer to as 'tapes'. These molecules represent a range of volumes and shapes that contain a common molecular fragment (DKP ring). We examined this series of compounds with three objectives in mind: (i) to establish the ability of the hydrogen-bonded 'tape' motif to persist through these differences in volume and shape; (ii) to provide a series of structurally related compounds to use to test computational methods of predicting crystal structure from molecular structure; (iii) to search for qualitative correlations between molecular structure and crystal packing. All compounds form tapes and with one exception, all tapes pack with their long axes parallel. When viewed down their long axis, two types of tapes emerge: planar and nonplanar. The type of tape that forms reflects the conformation adapted by the DKP ring-planar or boat. Planar tapes form when the angle (α) between the two planes defined by the cis-amides in the DKP ring is 180°; nonplanar tapes form when α 180°. Five of the eight compounds studied form planar tapes, the remaining three compounds form nonplanar tapes. Despite the variability in volume and shape represented by this series of molecules, the persistence of the tape motif in their crystalline solids suggests that the hydrogen-bonding interactions between parallel alignment of tapes that pack in a manner that permits the interdigitation of substituents on adjacent tapes.

Synthesis and tumorinhibiting activity of lanthanum(III) complexes with some 1-aminocycloalkancarboxylic acids

Complexes of La(III) with 1-aminocyclopentane-, -hexane, -heptane and -4-ethylcyclohexanecarboxylic acids were obtained. The compounds were characterized by elemental analyses, IR spectroscopy and conductivity measurements. The following general formula was derived: LaL3Cl3·5 H2O, where L is the corresponding 1-aminocycloalkanecarboxylic acid. The pharmacological studies showed that all complexes manifested higher cytostatic and cytotoxic effects in comparison with lanthanum chloride. Much higher cytotoxic (anti-P388/D1) and cytostatic (anti-L-1210 and antimelanoma-B16) activity was found for the lanthanum complex with 1-aminocyclopentanecarboxylic acid.

Peptide Sweeteners. 6. Structural Studies on the C-Terminal Amino Acid of L-Aspartyl Dipeptide Sweeteners

Stereochemical and structural aspects of the variations in the C-terminal residue of L-aspartyl-L-phenylalanine methyl ester have been investigated.Novel configurational analogues such as L-aspartyl-D-alanine benzyl ester and L-aspartyl-D-α-aminobutyric acid benzyl ester were found to be sweet.In addition, chiral and achiral α,α-dialkylglycine and α-aminocycloalkanecarboxylic acids were incorporated into the dipeptides.The L-aspartic acid based dipeptide derivatives of α-aminoisobutyric acid methyl ester, α-aminocyclopropanecarboxylic acid methyl ester, α-aminocyclobutanecarboxylic acid methyl ester, and α-aminocyclopentanecarboxylic acid methyl ester are sweet.Dipeptides with α-aminocyclohexanecarboxylic acid methyl ester and α-aminocycloheptanecarboxylic acid methyl ester are bitter, whereas the analogues with α-aminocyclooctanecarboxylic acid methyl ester, α,α-diethylglycine methyl ester, and α-aminoisobutyric acid benzyl ester are tasteless.Aspects on chirality and effective volume of the C-terminal residue are discussed and correlated with taste.