Azaspirene | CAS#461644-34-8 | angiogenesis inhibitor

MedKoo Cat#: 145565 | Name: Azaspirene

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Azaspirene is a novel angiogenesis inhibitor with a 1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione skeleton. Azaspirene was previously shown to inhibit human umbilical vein endothelial cell (HUVEC) migration induced by vascular endothelial growth factor (VEGF) at an effective dose. Azaspirene analogs may be effective against uterine carcinosarcoma, possibly acting via potent anti-angiogenic effects.

Chemical Structure

Azaspirene

CAS#461644-34-8

Theoretical Analysis

MedKoo Cat#: 145565

Name: Azaspirene

CAS#: 461644-34-8

Chemical Formula: C21H23NO5

Exact Mass: 369.1600

Molecular Weight: 369.42

Elemental Analysis: C, 68.28; H, 6.28; N, 3.79; O, 21.65

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

Azaspirene;

IUPAC/Chemical Name

(5S,8R,9R)-8-benzyl-2-((1E,3E)-hexa-1,3-dien-1-yl)-8,9-dihydroxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione

InChi Key

QLKGRMRPKQNCRR-XXPFWKOGSA-N

InChi Code

1S/C21H23NO5/c1-3-4-5-9-12-16-14(2)17(23)21(27-16)18(24)20(26,22-19(21)25)13-15-10-7-6-8-11-15/h4-12,18,24,26H,3,13H2,1-2H3,(H,22,25)/b5-4+,12-9+/t18-,20+,21+/m0/s1

SMILES Code

CC\C=C\C=C\C1=C(C)C(=O)[C@@]2(O1)[C@@H](O)[C@](O)(CC3=CC=CC=C3)NC2=O

Appearance

To be determined

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 -4 C for short term (days to weeks) or -20 C for long term(months to years).

Solubility

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 369.42 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Asami Y, Kakeya H, Komi Y, Kojima S, Nishikawa K, Beebe K, Neckers L, Osada H. Azaspirene, a fungal product, inhibits angiogenesis by blocking Raf-1 activation. Cancer Sci. 2008 Sep;99(9):1853-8. doi: 10.1111/j.1349-7006.2008.00890.x. Epub 2008 Jul 10. PMID: 18637013; PMCID: PMC2687096. 2: Kang T, Jo D, Han S. Six-Step Total Synthesis of Azaspirene. J Org Chem. 2017 Sep 15;82(18):9335-9341. doi: 10.1021/acs.joc.7b01224. Epub 2017 Aug 3. PMID: 28699341. 3: Emoto M, Yano K, Choijamts B, Sakai S, Hirasawa S, Wakamori S, Aizawa M, Nabeshima K, Tachibana K, Kanomata N. Azaspirene analogs inhibit the growth of human uterine carcinosarcoma in vitro and in vivo. Anticancer Res. 2015 May;35(5):2739-46. PMID: 25964553. 4: Asami Y, Kakeya H, Onose R, Yoshida A, Matsuzaki H, Osada H. Azaspirene: a novel angiogenesis inhibitor containing a 1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione skeleton produced by the fungus Neosartorya sp. Org Lett. 2002 Aug 22;4(17):2845-8. doi: 10.1021/ol020104+. PMID: 12182570. 5: Hirasawa S, Mukai K, Sakai S, Wakamori S, Hasegawa T, Souma K, Kanomata N, Ogawa N, Aizawa M, Emoto M. Elucidation of Racemization Process of Azaspirene Skeleton in Neutral Aqueous Media. J Org Chem. 2018 Dec 7;83(23):14457-14464. doi: 10.1021/acs.joc.8b02223. Epub 2018 Nov 13. PMID: 30381952. 6: Hayashi Y, Shoji M, Yamaguchi J, Sato K, Yamaguchi S, Mukaiyama T, Sakai K, Asami Y, Kakeya H, Osada H. Asymmetric total synthesis of (-)-azaspirene, a novel angiogenesis inhibitor. J Am Chem Soc. 2002 Oct 16;124(41):12078-9. doi: 10.1021/ja0276826. PMID: 12371831. 7: Ibrahim SRM, Mohamed GA, Al Haidari RA, El-Kholy AA, Zayed MF. Potential Anti-Malarial Agents from Endophytic Fungi: A Review. Mini Rev Med Chem. 2018;18(13):1110-1132. doi: 10.2174/1389557518666180305163151. PMID: 29512460. 8: Tsunematsu Y, Fukutomi M, Saruwatari T, Noguchi H, Hotta K, Tang Y, Watanabe K. Elucidation of pseurotin biosynthetic pathway points to trans-acting C-methyltransferase: generation of chemical diversity. Angew Chem Int Ed Engl. 2014 Aug 4;53(32):8475-9. doi: 10.1002/anie.201404804. Epub 2014 Jun 18. PMID: 24939566; PMCID: PMC4605568. 9: Warmuth R, Makowiec S. Photochemical and thermal reactions of intermediates in the phenylnitrene rearrangement inside a hemicarcerand. J Am Chem Soc. 2007 Feb 7;129(5):1233-41. doi: 10.1021/ja066130a. PMID: 17263406.