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129298-91-5,MFCD00870281
Catalog No.:AA000YZD

129298-91-5 | Carbamic acid, N-(2-chloroacetyl)-, (3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methyl-2-buten-1-yl)-2-oxiranyl]-1-oxaspiro[2.5]oct-6-yl ester

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5mg
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10mg
≥98%
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25mg
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA000YZD
Chemical Name:
Carbamic acid, N-(2-chloroacetyl)-, (3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methyl-2-buten-1-yl)-2-oxiranyl]-1-oxaspiro[2.5]oct-6-yl ester
CAS Number:
129298-91-5
Molecular Formula:
C19H28ClNO6
Molecular Weight:
401.8817
MDL Number:
MFCD00870281
SMILES:
CO[C@@H]1[C@@H](CC[C@@]2([C@H]1[C@@]1(C)O[C@@H]1CC=C(C)C)CO2)OC(=O)NC(=O)CCl
NSC Number:
642492
Properties
Computed Properties
 
Complexity:
636  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
6  
Heavy Atom Count:
27  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
7  
XLogP3:
2.5  

Downstream Synthesis Route
122734-32-1    129298-91-5   
C27H45N3O8 

[1]Patent:US2014/308235,2014,A1.Locationinpatent:Paragraph0362;0363

[2]Patent:US9320805,2016,B2.Locationinpatent:Page/Pagecolumn63-64

[3]Patent:US2017/258925,2017,A1.Locationinpatent:Paragraph0226;0227

Literature

Title: Pyridinylquinazolines selectively inhibit human methionine aminopeptidase-1 in cells.

Journal: Journal of medicinal chemistry 20130523

Title: The angiogenic inhibitor TNP-470 decreases caloric intake and weight gain in high-fat fed mice.

Journal: Obesity (Silver Spring, Md.) 20121001

Title: Disruption of Wnt planar cell polarity signaling by aberrant accumulation of the MetAP-2 substrate Rab37.

Journal: Chemistry & biology 20111028

Title: Synthesis and antitumor activity of 1,2,4-triazoles having 1,4-benzodioxan fragment as a novel class of potent methionine aminopeptidase type II inhibitors.

Journal: Bioorganic & medicinal chemistry 20111015

Title: Temporal changes in microvessel leakiness during wound healing discriminated by in vivo fluorescence recovery after photobleaching.

Journal: The Journal of physiology 20111001

Title: Metronomic doxifluridine chemotherapy combined with the anti-angiogenic agent TNP-470 inhibits the growth of human uterine carcinosarcoma xenografts.

Journal: Cancer science 20110801

Title: Enhanced anti-tumor activity and safety profile of targeted nano-scaled HPMA copolymer-alendronate-TNP-470 conjugate in the treatment of bone malignances.

Journal: Biomaterials 20110701

Title: Identification, structural properties and chelating capacity of miltipolone as a broad-spectrum inhibitor to cancer cells.

Journal: European journal of medicinal chemistry 20110401

Title: Circulating endothelial progenitor cells are up-regulated in a mouse model of endometriosis.

Journal: The American journal of pathology 20110401

Title: Effect of nitroxoline on angiogenesis and growth of human bladder cancer.

Journal: Journal of the National Cancer Institute 20101215

Title: Inhibitory effects of TNP-470 in combination with BCNU on tumor growth of human glioblastoma xenografts.

Journal: Journal of Huazhong University of Science and Technology. Medical sciences = Hua zhong ke ji da xue xue bao. Yi xue Ying De wen ban = Huazhong keji daxue xuebao. Yixue Yingdewen ban 20101201

Title: Reversal of TNP-470-induced endothelial cell growth arrest by guanine and guanine nucleosides.

Journal: The Journal of pharmacology and experimental therapeutics 20100901

Title: Synthesis and inhibitory evaluation of cyclohexen-2-yl- and cyclohexyl-substituted phenols and quinones to endothelial cell and cancer cells.

Journal: European journal of medicinal chemistry 20100601

Title: An in vitro model that can distinguish between effects on angiogenesis and on established vasculature: actions of TNP-470, marimastat and the tubulin-binding agent Ang-510.

Journal: Biochemical and biophysical research communications 20100108

Title: Broad spectrum antiangiogenic treatment for ocular neovascular diseases.

Journal: PloS one 20100101

Title: Structure of a microsporidian methionine aminopeptidase type 2 complexed with fumagillin and TNP-470.

Journal: Molecular and biochemical parasitology 20091201

Title: Antiparasitic activities of novel, orally available fumagillin analogs.

Journal: Bioorganic & medicinal chemistry letters 20090901

Title: Maternal administration of anti-angiogenic agents, TNP-470 and Angiostatin4.5, induces fetal microphthalmia.

Journal: Molecular vision 20090101

Title: TX-2152: a conformationally rigid and electron-rich diyne analogue of FTY720 with in vivo antiangiogenic activity.

Journal: Bioorganic & medicinal chemistry 20080815

Title: An orally delivered small-molecule formulation with antiangiogenic and anticancer activity.

Journal: Nature biotechnology 20080701

Title: Anti-tumor effect of angiogenesis inhibitor TNP-470 and 5-FU combined therapy on human gastric cancer xenograft.

Journal: Hepato-gastroenterology 20080101

Title: The bisphosphonate, zoledronic acid reduces experimental neuroblastoma growth by interfering with tumor angiogenesis.

Journal: Anticancer research 20080101

Title: Judah Folkman's contribution to the inhibition of angiogenesis.

Journal: Lymphatic research and biology 20080101

Title: Malignant progression and blockade of angiogenesis in a murine transgenic model of neuroblastoma.

Journal: Cancer research 20071001

Title: Changes in the antioxidant system by TNP-470 in an in vivo model of hepatocarcinoma.

Journal: Translational research : the journal of laboratory and clinical medicine 20070901

Title: Highly potent inhibitors of methionine aminopeptidase-2 based on a 1,2,4-triazole pharmacophore.

Journal: Journal of medicinal chemistry 20070809

Title: Anti-tumor action of tumor necrosis factor against Bomirski Ab melanoma in hamsters.

Journal: Archivum immunologiae et therapiae experimentalis 20070801

Title: Angiogenesis inhibition as a therapeutic approach for inflammatory synovitis.

Journal: Nature clinical practice. Rheumatology 20070801

Title: Fumagillin: an anti-infective as a parent molecule for novel angiogenesis inhibitors.

Journal: Expert review of anti-infective therapy 20070801

Title: Antitumor effect of TNP-470, an angiogenesis inhibitor, combined with ultrasound irradiation for human uterine sarcoma xenografts evaluated using contrast color Doppler ultrasound.

Journal: Cancer science 20070601

Title: Tumor cytotoxicity and endothelial Rac inhibition induced by TNP-470 in anaplastic thyroid cancer.

Journal: Molecular cancer therapeutics 20070401

Title: Assessment of the anti-obesity effects of the TNP-470 analog, CKD-732.

Journal: Journal of molecular endocrinology 20070401

Title: Genetic analysis of high-metastatic clone of RCT sarcoma in mice, and its growth regression in vivo in response to angiogenesis inhibitor TNP-470.

Journal: Journal of experimental & clinical cancer research : CR 20070301

Title: Cell-cycle inhibition by TNP-470 in an in vivo model of hepatocarcinoma is mediated by a p53 and p21WAF1/CIP1 mechanism.

Journal: Translational research : the journal of laboratory and clinical medicine 20070101

Title: Inhibition of expression of vascular endothelial growth factor and its receptors in pulmonary adenocarcinoma cell by TNP-470 in combination with gemcitabine.

Journal: Journal of Zhejiang University. Science. B 20061001

Title: Fumarranol, a rearranged fumagillin analogue that inhibits angiogenesis in vivo.

Journal: Journal of medicinal chemistry 20060921

Title: A noncanonical path to mechanism of action.

Journal: Chemistry & biology 20060901

Title: A chemical and genetic approach to the mode of action of fumagillin.

Journal: Chemistry & biology 20060901

Title: Fumagillin suppresses HIV-1 infection of macrophages through the inhibition of Vpr activity.

Journal: FEBS letters 20060515

Title: TNP-470 blockage of VEGF synthesis is dependent on MAPK/COX-2 signaling pathway in PDGF-BB-activated hepatic stellate cells.

Journal: Biochemical and biophysical research communications 20060303

Title: Inhibition of rat urinary bladder carcinogenesis by the antiangiogenic drug TNP-470.

Journal: Asian Pacific journal of cancer prevention : APJCP 20060101

Title: The atypical pattern of cell death in B16F10 melanoma cells treated with TNP-470.

Journal: Cellular & molecular biology letters 20060101

Title: Combination therapy with tumor-lysate pulsed dendritic cells and antiangiogenic drug TNP-470 for mouse pancreatic cancer.

Journal: International journal of cancer 20051110

Title: Antiangiogenic drugs for chemotherapy of bladder tumours.

Journal: Chemotherapy 20051001

Title: A novel mechanism of action of the fumagillin analog, TNP-470, in the B16F10 murine melanoma cell line.

Journal: Anti-cancer drugs 20050901

Title: Total synthesis and antiangiogenic activity of cyclopentane analogues of fumagillol.

Journal: Bioorganic & medicinal chemistry letters 20050801

Title: Roxithromycin inhibits constitutive activation of nuclear factor {kappa}B by diminishing oxidative stress in a rat model of hepatocellular carcinoma.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20050801

Title: Novel inhibitors targeted to methionine aminopeptidase 2 (MetAP2) strongly inhibit the growth of cancers in xenografted nude model.

Journal: International journal of cancer 20050310

Title: Synergistic inhibition of tumor growth and metastasis by combined treatment with TNP-470 and docetaxel in a human prostate cancer PC-3 model.

Journal: International journal of oncology 20050301

Title: Antiangiogenic strategies in neuroblastoma.

Journal: Cancer treatment reviews 20050201

Title: Inhibition of tumor angiogenesis during cisplatin chemotherapy for bladder cancer improves treatment outcome.

Journal: Urology 20050201

Title: Acceleration of follicular development by administration of vascular endothelial growth factor in cycling female rats.

Journal: The Journal of reproduction and development 20050201

Title: Antiangiogenic therapy for human pancreatic carcinoma xenografts in nude mice.

Journal: World journal of gastroenterology 20050121

Title: Roxithromycin inhibits angiogenesis of human hepatoma cells in vivo by suppressing VEGF production.

Journal: Anticancer research 20050101

Title: Pharmacokinetic model-predicted anticancer drug concentrations in human tumors.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20041201

Title: TNP-470, an angiogenesis inhibitor, attenuates the development of allograft vasculopathy.

Journal: Transplantation 20041027

Title: Synergistic inhibition of tumor growth and metastasis by combined treatment with TNP-470 and gemcitabine in a human bladder cancer KoTCC-1 model.

Journal: The Journal of urology 20041001

Title: TNP-470, an angiogenesis inhibitor, suppresses the progression of peritoneal fibrosis in mouse experimental model.

Journal: Kidney international 20041001

Title: Participation of cyclin D1 deregulation in TNP-470-mediated cytostatic effect: involvement of senescence.

Journal: Biochemical pharmacology 20040815

Title: Angiogenesis inhibitor, TNP-470, prevents diet-induced and genetic obesity in mice.

Journal: Circulation research 20040625

Title: A quadruple therapy synergistically blocks proliferation and promotes apoptosis of hepatoma cells.

Journal: Oncology reports 20040501

Title: A single amino acid residue defines the difference in ovalicin sensitivity between type I and II methionine aminopeptidases.

Journal: The Journal of biological chemistry 20040305

Title: Targeting angiogenesis with a conjugate of HPMA copolymer and TNP-470.

Journal: Nature medicine 20040301

Title: TNP-470 promotes initial vascular sprouting in xenograft tumors.

Journal: Molecular cancer therapeutics 20040301

Title: cis-Diamminedichloroplatinum-resistant cell lines derived from human epithelial ovarian carcinoma express increased susceptibility to angiogenesis inhibitor TNP-470.

Journal: Gynecologic oncology 20040201

Title: Absorption, distribution, metabolism, and excretion of CKD-732, a novel antiangiogenic fumagillin derivative, in rats, mice, and dogs.

Journal: Archives of pharmacal research 20040201

Title: Carcinosarcoma-induced endothelial cells tube formation through KDR/Flk-1 is blocked by TNP-470.

Journal: Cancer letters 20040108

Title: Investigation of novel fumagillin analogues as angiogenesis inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20040105

Title: Angiogenesis inhibition by angiostatin, endostatin and TNP-470 prevents cyclophosphamide induced cystitis.

Journal: Angiogenesis 20040101

Title: Small molecule inhibitors of methionine aminopeptidase type 2 (MetAP-2).

Journal: Angiogenesis 20040101

Title: The combination of antiangiogenic and cytotoxic agents in the treatment of prostate cancer.

Journal: Clinical prostate cancer 20031201

Title: Tumor suppression by a rationally designed reversible inhibitor of methionine aminopeptidase-2.

Journal: Cancer research 20031115

Title: [Systemic treatment for hepatocellular carcinoma].

Journal: Zentralblatt fur Chirurgie 20031101

Title: Changes in tumor vascularization after irradiation, anthracyclin, or antiangiogenic treatment in nitrosomethyl ureas-induced rat mammary tumors.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20031001

Title: Angiogenesis inhibitors target the endothelial cell cytoskeleton through altered regulation of heat shock protein 27 and cofilin.

Journal: Cancer research 20031001

Title: Effects of angiogenesis inhibitor TNP-470 on the development of uterine adenomyosis in mice.

Journal: Fertility and sterility 20030901

Title: Homology modeling and calculation of the cobalt cluster charges of the Encephazlitozoon cuniculi methionine aminopeptidase, a potential target for drug design.

Journal: Biophysical chemistry 20030801

Title: TNP-470 inhibits oxidative stress, nitric oxide production and nuclear factor kappa B activation in a rat model of hepatocellular carcinoma.

Journal: Free radical research 20030801

Title: Role of host angiotensin II type 1 receptor in tumor angiogenesis and growth.

Journal: The Journal of clinical investigation 20030701

Title: TNP-470 inhibits 7,12-dimethylbenz[a]anthracene-induced mammary tumor formation when administered before the formation of carcinoma in situ but is not additive with tamoxifen.

Journal: Laboratory investigation; a journal of technical methods and pathology 20030701

Title: Angiogenesis inhibitor TNP-470 (AGM-1470) suppresses vascular smooth muscle cell proliferation after balloon injury in rats.

Journal: The Journal of surgical research 20030615

Title: 'Vasocrine' formation of tumor cell-lined vascular spaces: implications for rational design of antiangiogenic therapies.

Journal: Cancer research 20030601

Title: Effect of angiogenesis inhibitor TNP-470 on the growth, blood flow, and microvessel density in xenografts of human uterine carcinosarcoma in nude mice.

Journal: Gynecologic oncology 20030401

Title: Angiogenesis inhibition with TNP-470, 2-methoxyestradiol, and paclitaxel in experimental pancreatic carcinoma.

Journal: Pancreas 20030301

Title: Preparation of poly-lactic acid microspheres containing the angiogenesis inhibitor TNP-470 with medium-chain triglyceride and the in vitro evaluation of release profiles.

Journal: European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V 20030301

Title: Concise stereocontrolled routes to fumagillol, fumagillin, and TNP-470.

Journal: Chirality 20030201

Title: In vivo chamber angiogenesis assay: an optimized Matrigel plug assay for fast assessment of anti-angiogenic activity.

Journal: International journal of oncology 20030201

Title: Optimizing the dosing schedule of TNP-470 [O-(chloroacetyl-carbamoyl) fumagillol] enhances its antitumor and antiangiogenic efficacies.

Journal: The Journal of pharmacology and experimental therapeutics 20030201

Title: Docetaxel enhances the therapeutic effect of the angiogenesis inhibitor TNP-470 (AGM-1470) in metastatic human transitional cell carcinoma.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20030201

Title: [Inhibitory effects of TNP-470 in combination with 5-fluorouracil on growth of human colon cancer].

Journal: Ai zheng = Aizheng = Chinese journal of cancer 20021201

Title: [Experimental therapy with angiogenesis inhibitor TNP-470 on human ovarian cancer transplanted subcutaniously in nude mice].

Journal: Zhonghua fu chan ke za zhi 20020901

Title: Enhanced suppression of prostate tumor growth by combining C-CAM1 gene therapy and angiogenesis inhibitor TNP-470.

Journal: Anti-cancer drugs 20020801

Title: Augmented antitumour effects of combination therapy with TNP-470 and chemoimmunotherapy in mice.

Journal: Journal of cancer research and clinical oncology 20020801

Title: Angiogenesis inhibitors in lung cancer.

Journal: Current oncology reports 20020701

Title: Novel bicyclic oxazolone derivatives as anti-angiogenic agents.

Journal: Bioorganic & medicinal chemistry letters 20020603

Title: Angiogenesis in bladder cancer--prognostic marker and target for future therapy.

Journal: Surgical oncology 20020601

Title: Antitumor effect of TNP-470 is not associated to decrease of angiogenesis in an experimental malignant neuroectodermic tumor.

Journal: Journal of neuro-oncology 20020601

Title: CHS 828 inhibits neuroblastoma growth in mice alone and in combination with antiangiogenic drugs.

Journal: Pediatric research 20020501

Title: Assay of TNP-470 and its two major metabolites in human plasma by high-performance liquid chromatography-mass spectrometry.

Journal: Journal of chromatographic science 20020401

Title: Injection of antiangiogenic agents into the macaque preovulatory follicle: disruption of corpus luteum development and function.

Journal: Endocrine 20020401

Title: Angiogenesis inhibitors specific for methionine aminopeptidase 2 as drugs for malaria and leishmaniasis.

Journal: Journal of biomedical science 20020101

Title: [Human microsporidiosis].

Journal: Klinische Padiatrie 20020101

Title: The role of growth factors, angiogenic enzymes and apoptosis in neovascularization and tumor growth-collected publications.

Journal: Verhandelingen - Koninklijke Academie voor Geneeskunde van Belgie 20020101

Title: TNP-470 combined with nicardipine suppresses in vivo growth of PC-3, a human prostate cancer cell line.

Journal: Urologic oncology 20020101

Title: QSAR of the inhibition of angiogenesis by TNP-470 and ovalicin analogues: another example of an allosteric interaction.

Journal: Bioorganic & medicinal chemistry 20011201

Title: TNP-470 reduces collagen and macrophage accumulation in expanded polytetrafluoroethylene tube implants.

Journal: The Journal of surgical research 20011101

Title: A potential use of a synthetic retinoid TAC-101 as an orally active agent that blocks angiogenesis in liver metastases of human stomach cancer cells.

Journal: Japanese journal of cancer research : Gann 20011101

Title: Drug targeting to choroidal neovascularization.

Journal: Advanced drug delivery reviews 20011031

Title: Inhibition of inflammatory corneal angiogenesis by TNP-470.

Journal: Investigative ophthalmology & visual science 20011001

Title: The inhibitory effects of TNP470 on tumour growth of head and neck carcinoma cell producing interleukin-8.

Journal: The Journal of laryngology and otology 20011001

Title: Pharmacodynamic-mediated reduction of temozolomide tumor concentrations by the angiogenesis inhibitor TNP-470.

Journal: Cancer research 20010715

Title: Phase I trial of the angiogenesis inhibitor TNP-470 for progressive androgen-independent prostate cancer.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20010501

Title: General aspects of anti-angiogenesis and cancer therapy.

Journal: Expert opinion on biological therapy 20010301

Title: In vivo antitumor effect of vascular targeting combined with either ionizing radiation or anti-angiogenesis treatment.

Journal: International journal of radiation oncology, biology, physics 20010201

Title: Effect of TNP-470 (AGM-1470) on the growth of rat rhabdomyosarcoma tumors of different sizes.

Journal: Cancer investigation 20010101

Title: Regulation and action of angiogenic factors in the primate ovary.

Journal: Archives of medical research 20010101

Title: Treatment of tamoxifen-refractory breast cancer--approach by animal models.

Journal: Breast cancer (Tokyo, Japan) 20010101

Title: A re-evaluation of fumagillin selectivity towards endothelial cells.

Journal: Anticancer research 20010101

Title: Microsporidian methionine aminopeptidase type 2.

Journal: The Journal of eukaryotic microbiology 20010101

Title: In vitro and in vivo evaluation of aminopeptidase inhibitors as antimicrosporidial therapies.

Journal: The Journal of eukaryotic microbiology 20010101

Title: Antiangiogenic and antitumour effects in vivo of genistein applied alone or combined with cyclophosphamide.

Journal: Anticancer research 20010101

Title: Antiangiogenic scheduling of chemotherapy improves efficacy against experimental drug-resistant cancer.

Journal: Cancer research 20000401

Title: TNP-470 is an effective antimicrosporidial agent.

Journal: The Journal of infectious diseases 19980201

Title: Screening of compounds for antimicrosporidial activity in vitro.

Journal: Folia parasitologica 19980101

Title: Effects of albendazole, fumagillin, and TNP-470 on microsporidial replication in vitro.

Journal: Antimicrobial agents and chemotherapy 19970701

Title: Synthetic analogues of fumagillin that inhibit angiogenesis and suppress tumour growth.

Journal: Nature 19901206

Title: Kidoikhammouan S, et al. TNP-470, a methionine aminopeptidase-2 inhibitor, inhibits cell proliferation, migration and invasion of human cholangiocarcinoma cells in vitro. Asian Pac J Cancer Prev. 2012;13 Suppl:155-60.

Title: White HM, et al. The angiogenic inhibitor TNP-470 decreases caloric intake and weight gain in high-fat fed mice. Obesity (Silver Spring). 2012 Oct;20(10):2003-9.

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Tags:129298-91-5 Molecular Formula|129298-91-5 MDL|129298-91-5 SMILES|129298-91-5 Carbamic acid, N-(2-chloroacetyl)-, (3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methyl-2-buten-1-yl)-2-oxiranyl]-1-oxaspiro[2.5]oct-6-yl ester