N-甲基胞嘧啶

化合物

N-甲基胞嘧啶1-甲基胞嘧啶(簡寫:dS)是DNA鹼基胞嘧啶C)的甲基化產物。N-甲基胞嘧啶可由胞嘧啶碘甲烷在一定條件下反應得到[4]硫酸二甲酯[5]三甲基氫氧化鋶[6]也能作為甲基化試劑。

N-甲基胞嘧啶
IUPAC名
4-amino-1-methyl-2(1H)-pyrimidinone
識別
CAS號 1122-47-0  checkY
PubChem 79143
ChemSpider 71474
SMILES
 
  • CN1C=CC(=NC1=O)N
InChI
 
  • 1S/C5H7N3O/c1-8-3-2-4(6)7-5(8)9/h2-3H,1H3,(H2,6,7,9)
InChIKey HWPZZUQOWRWFDB-UHFFFAOYSA-N
ChEBI 39624
MeSH 1-Methylcytosine
性質
化學式 C5H7N3O
摩爾質量 125.13 g·mol−1
密度 1.4483 g·cm−3[1]
熔點 278—279 °C(551—552 K)[2]
沸點 300—303 °C(573—576 K)(分解)[3]
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。

參考文獻

  1. ^ M. Rossi, T. J. Kistenmacher. 1-Methylcytosine: a refinement. Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry. 1977-12-01, 33 (12): 3962–3965 [2019-03-18]. ISSN 0567-7408. doi:10.1107/S0567740877012618. (原始內容存檔於2018-06-02). 
  2. ^ Johnson, T. B.; Clapp, S. H. Researches on Pyrimidines XXXIII: Syntheses of Some N Alkyl Derivatives of Cytosine, Thymine and Uracil. Journal of Biological Chemistry, 1909. 5: 49-70. ISSN: 0021-9258.
  3. ^ Ramachandra S. Hosmane, Nelson J. Leonard. Simple Convenient Synthesis of 1-Methylcytosine. Synthesis. 1981, 1981 (02): 118–119 [2019-03-18]. ISSN 0039-7881. doi:10.1055/s-1981-29352. (原始內容存檔於2018-06-04) (英語). 
  4. ^ Steffi Noll, Marijeta Kralj, Lidija Šuman, Holger Stephan, Ivo Piantanida. Synthesis of modified pyrimidine bases and positive impact of chemically reactive substituents on their in vitro antiproliferative activity. European Journal of Medicinal Chemistry. 2009-3, 44 (3): 1172–1179 [2019-03-18]. doi:10.1016/j.ejmech.2008.06.002. (原始內容存檔於2018-06-29) (英語). 
  5. ^ Bredereck, Hellmut; Haas, Hans; Martini, Annelise. Nucleic acids. XXIII. Methylated nucleosides and purines and their pharmacological effects. 2. Methylation of nucleosides with dimethyl sulfate. Chemische Berichte, 1948. 81: 307-313. ISSN: 0009-2940.
  6. ^ Kiyoshi Yamauchi, Toshizumi Tanabe, Masayoshi Kinoshita. Trimethylsulfonium hydroxide: a new methylating agent. The Journal of Organic Chemistry. 1979-2, 44 (4): 638–639 [2019-03-18]. ISSN 0022-3263. doi:10.1021/jo01318a037. (原始內容存檔於2019-10-18) (英語).