2-(S,N-acetyl cysteaminyl) acetic acid methyl ester | 152844-26-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(S,N-acetyl cysteaminyl) acetic acid methyl ester
• 英文别名: Methyl 2-(2-acetamidoethylsulfanyl)acetate
• CAS: 152844-26-3
• 化学式: C₇H₁₃NO₃S
• mdl: MFCD24388441
• 分子量: 191.251
• InChiKey: SYFQQEZTGHOJMN-UHFFFAOYSA-N

物化性质

• 沸点：
  359.5±27.0 °C(predicted)
• 密度：
  1.141±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.714
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(S,N-acetyl cysteaminyl) acetic acid methyl ester 以 neat (no solvent) 为溶剂， 反应 10.5h， 生成 N¹-<2-(S,N-acetyl cysteaminyl) acetyl> spermidine amide ditrifluoroacetate
  参考文献：
  名称：

  Regioselective synthesis of inhibitors of histone acetyl transferase covalently linking spermidine to the s-terminus of coenzyme a and fragments.

  摘要：

  The reaction of a bromoacetylthioester BrCH2CO-S-R (R radical in the coenzyme A series) with spermidine (Spd) derivatives is investigated and it is established that the adduct SpdCOCH2-S-R 1 is the product of the reaction. Parallel studies with model compounds show that this is a general reaction of bromoacetylthioesters. The synthesis of analogs of 1 is described and they correspond to inhibitors of the histone acetyltransferase.

  DOI：

  10.1016/s0040-4020(01)80153-8
• 作为产物：
  描述：

  N-acetyl S-(2-bromoacetyl) cysteamine thioester 在 氢氧化钾 作用下， 以 甲醇 、 乙醚 、 乙醇 为溶剂， 反应 1.0h， 生成 2-(S,N-acetyl cysteaminyl) acetic acid methyl ester
  参考文献：
  名称：

  Regioselective synthesis of inhibitors of histone acetyl transferase covalently linking spermidine to the s-terminus of coenzyme a and fragments.

  摘要：

  The reaction of a bromoacetylthioester BrCH2CO-S-R (R radical in the coenzyme A series) with spermidine (Spd) derivatives is investigated and it is established that the adduct SpdCOCH2-S-R 1 is the product of the reaction. Parallel studies with model compounds show that this is a general reaction of bromoacetylthioesters. The synthesis of analogs of 1 is described and they correspond to inhibitors of the histone acetyltransferase.

  DOI：

  10.1016/s0040-4020(01)80153-8

文献信息

• METHODS OF INCREASING THE CYTOTOXICITY OF CHEMOTHERAPEUTIC AGENTS WITH MULTISUBSTRATE INHIBITORS OF HISTONE, PROTEIN-LYS, POLYAMINE ACETYLATION, AND POLYAMINE METABOLISM
  申请人：Vanderbilt University

  公开号：US20160243063A1

  公开（公告）日：2016-08-25

  A method of treating cancer in a subject in need thereof, comprising administering to the subject a first amount of a compound of the HAT inhibitor of the following formula: wherein R is chosen from coenzyme A, (CH 2 ) 2 NHCO(CH 2 ) 2 NHCOR 2 ; (CH 2 ) 2 NHCOR 3 ; (CH 2 ) 2 NHCO(CH 2 ) 2 NHCOR 4 ; R 1 is H, NH 2 , NH, N, and R 1 can optionally cyclize with at least one other X 2 to form a C 3-8 membered ring containing C, O, S, or N; R 2 is chosen from alkyl, cycloalkyl, aryl, heteroaryl; R 3 is chosen from an alkyl, cycloalkyl, aryl, heteroaryl; R 4 is chosen from CH(OH)C(CH 3 ) 2 CH 2 )OCOR 2 ; X 1 is chosen from H or can cyclize with one other X 2 or R 1 to form a C 3-8 membered ring containing C, O, S, or N; and X 2 is chosen from C, N, NH, and can optionally cyclize with at least one other X 2 or R 1 to form a C 3-8 membered ring containing C, O, S, or N; or a pharmaceutically acceptable salt or hydrate thereof, thereby treating the cancer.

  一种治疗需要的患者体内癌症的方法，包括向患者投予以下式的HAT抑制剂化合物的第一量：其中R从辅酶A、(CH2)2NHCO(CH2)2NHCOR2；(CH2)2NHCOR3；(CH2)2NHCO(CH2)2NHCOR4中选择；R1为H、NH2、NH、N，且R1可以选择与至少另一个X2环化以形成含有C、O、S或N的C3-8环的环；R2从烷基、环烷基、芳基、杂环烷基中选择；R3从烷基、环烷基、芳基、杂环烷基中选择；R4从CH(OH)C(CH3)2CH2)OCOR2中选择；X1从H中选择，或者可以与另一个X2或R1环化以形成含有C、O、S或N的C3-8环；X2从C、N、NH中选择，或者可以选择与至少另一个X2或R1环化以形成含有C、O、S或N的C3-8环；或其药用盐或水合物，从而治疗癌症。
• US9107879B1
  申请人：——

  公开号：US9107879B1

  公开（公告）日：2015-08-18
• Regioselective synthesis of inhibitors of histone acetyl transferase covalently linking spermidine to the s-terminus of coenzyme a and fragments.
  作者：Georges Roblot、Renée Wylde、Aimée Martin、Joseph Parello

  DOI：10.1016/s0040-4020(01)80153-8

  日期：1993.1

  The reaction of a bromoacetylthioester BrCH2CO-S-R (R radical in the coenzyme A series) with spermidine (Spd) derivatives is investigated and it is established that the adduct SpdCOCH2-S-R 1 is the product of the reaction. Parallel studies with model compounds show that this is a general reaction of bromoacetylthioesters. The synthesis of analogs of 1 is described and they correspond to inhibitors of the histone acetyltransferase.