9-thioxanthone oxime 10,10-dioxide | 5395-25-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻喃类
• 英文名称: 9-thioxanthone oxime 10,10-dioxide
• 英文别名: 9-Oximino-thioxanthen-10,10-dioxid；10,10-dioxo-10H-10λ⁶-thioxanthen-9-one oxime；10,10-dioxo-10λ⁶-thioxanthen-9-one oxime；10,10-Dioxo-10λ⁶-thioxanthen-9-on-oxim；10-Thiaxanthenone,5-dioxide, oxime；N-(10,10-dioxothioxanthen-9-ylidene)hydroxylamine
• CAS: 5395-25-5
• 化学式: C₁₃H₉NO₃S
• 分子量: 259.285
• InChiKey: MFVFIUCBCLRVGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.1
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  9-thioxanthone oxime 10,10-dioxide 在 盐酸 、 氢氧化钾 、 PPA 作用下， 以 甲醇 为溶剂， 生成 3-(5,5,11-trioxo-5,11-dihydro-5λ6-dibenzo[b,f][1,4]thiazepin-10-yl)-propionic acid methyl ester
  参考文献：
  名称：

  Catsoulacos,P., Bulletin de la Societe Chimique de France, 1973, p. 2136 - 2137

  摘要：

  DOI：
• 作为产物：
  描述：

  10,10-二氧代噻吨-9-酮 在 盐酸羟胺 作用下， 以 乙醇 为溶剂， 生成 9-thioxanthone oxime 10,10-dioxide
  参考文献：
  名称：

  Oxime esters of anthraquinone as photo-induced DNA-cleaving agents for single- and double-strand scissions

  摘要：

  Anthraquinone-O-9-(4-cyanobenzoyl)oxime (13) with binding constant of 4.49x 10(4) M-1 exhibited single-strand scission of DNA at the concentration of 10 muM and double-strand scission at 50 muM upon UV irradiation. (C) 2003 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(03)00375-7

文献信息

• New Approach to Biomimetic Transamination Using Bifunctional [1,3]-Proton Transfer Catalysis in Thioxanthenyl Dioxide Imines
  作者：Anders Hjelmencrantz、Ulf Berg

  DOI：10.1021/jo0106748

  日期：2002.5.1

  A pyridoxamine equivalent, 9-aminothioxanthene 10,10-dioxide, has been designed that is capable of affording transamination in good to excellent yields of natural as well as artificial amino acids. Amidines and guanidines in catalytic amounts were capable of performing [1,3]-proton transfer in the imines under mild conditions, whereas various simple amines failed. The use of chiral catalysts resulted in modest asymmetric induction (ee less than or equal to 45%). The electronic dependence in para-substituted phenyl glyoxylate imines, isotope effects, and computational studies support a stepwise, bifunctional mechanism for amidine and guanidine catalysts. Attempts toward an autocatalytic model system are described.
• Catsoulacos, P.; Pelecanou, M.; Camoutsis, Ch., Journal of Heterocyclic Chemistry, 1991, vol. 28, # 5, p. 1437 - 1440
  作者：Catsoulacos, P.、Pelecanou, M.、Camoutsis, Ch.

  DOI：——

  日期：——
• Beckmann Rearrangement of Some Cyclic Sulfone Ketoximes¹
  作者：WILLIAM E. TRUCE、JOHN A. SIMMS

  DOI：10.1021/jo01357a007

  日期：1957.6
• Catsoulacos, Journal of Heterocyclic Chemistry, 1967, vol. 4, p. 645,646
  作者：Catsoulacos

  DOI：——

  日期：——
• Relationship Between Structure of Conjugated Oxime Esters and Their Ability to Cleave DNA
  作者：Jih Ru Hwu、Shwu-Chen Tsay、Shih Chin Hong、Ming-Hua Hsu、Chih-Fen Liu、Shang-Shing P. Chou

  DOI：10.1021/bc400060h

  日期：2013.11.20

  The size and geometry of polycycles are critical to intercalation into DNA. This work involves the establishment of a new compound library that includes 35 O-benzoyl oxime esters with intercalators of five types. These conjugated compounds were synthesized by the condensation of substituted benzoyl chlorides (XC6H4COCl; X = H, Me, CN, F, and NO2) or naphthoyl chlorides with oximes of fluoren-9-one, 9,10-anthraquinone, xanthen-9-one, thioxanthen-9-one, and 9H-thioxanthen-9-one, 10,10-dioxide to give the corresponding esters in 80-99% yields. All of these compounds could cleave DNA when photolyzed by UV light. Of these conjugates, 9,10-anthraquinone-O-9-(4-fluorobenzoyl)oxime with a binding constant of 4.49 x 10(4) M-1 cleaved DNA most efficiently. Examination of the structure activity relationship supports a conclusion that two factors affect DNA-cleaving potency. These are (1) the planarity of the intercalating moiety, and (2) the size and substituents of the benzoyl ring. The DNA-cleaving ability followed the order 9,10-anthraquinone > fluoren-9-one >= xanthen-9-one similar to thioxanthen-9-one > 9H-thioxanthen-9-one 10,10-dioxide. The benzoyl-containing oxime ester conjugates were more active than the corresponding naphthoyl-containing conjugates. The potency that was associated with the different substituents on the benzoyl ring followed the order F > CN >= NO2 > Me similar to H.