(2-methyl-indol-3-yl)-glyoxylic acid | 62454-47-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (2-methyl-indol-3-yl)-glyoxylic acid
• 英文别名: (2-Methyl-indol-3-yl)-glyoxylsaeure；2-(2-methyl-1H-indol-3-yl)-2-oxoacetic acid
• CAS: 62454-47-1
• 化学式: C₁₁H₉NO₃
• mdl: MFCD10686657
• 分子量: 203.197
• InChiKey: IYLDJJZSHNIIOQ-UHFFFAOYSA-N

物化性质

• 沸点：
  427.0±37.0 °C(Predicted)
• 密度：
  1.408±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  70.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2-methyl-indol-3-yl)-glyoxylic acid 生成 2-甲基吲哚-3-甲醛
  参考文献：
  名称：

  Oddo; Albanese, Gazzetta Chimica Italiana, 1927, vol. 57, p. 827,830

  摘要：

  DOI：
• 作为产物：
  描述：

  2,2,2-三氯-1-(2-甲基-吲哚-3-基)-乙酮 在 potassium carbonate 作用下， 生成 (2-methyl-indol-3-yl)-glyoxylic acid
  参考文献：
  名称：

  Sanna, Gazzetta Chimica Italiana, 1931, vol. 61, p. 60,71

  摘要：

  DOI：

文献信息

• A convenient method for the synthesis of indole-3-acetic acids
  作者：Xiangming Guan、Ronald T. Borchardt

  DOI：10.1016/s0040-4039(00)76815-8

  日期：1994.5

  Starting from the corresponding indoles, indole-3-acetic acids were synthesized through indole-3-glyoxylic acids, followed by hydrazone formation with p-toluenesulfonhydrazide, then reduction of the hydrazones with sodium borohydride.

  从相应的吲哚开始，通过吲哚-3-乙醛酸合成吲哚-3-乙酸，然后与对甲苯磺酰肼形成，然后用硼氢化钠还原hydr。
• Synthetic analogs of indole-containing natural products as inhibitors of sortase A and isocitrate lyase
  作者：Yeon-Ju Lee、Yu-Ri Han、Wanki Park、Seo-Hee Nam、Ki-Bong Oh、Hyi-Seung Lee

  DOI：10.1016/j.bmcl.2010.10.029

  日期：2010.12

  Guided by the inhibitory activities of indole-containing natural products against isocitrate lyase (ICL) from Candida albicans and sortase A (SrtA) from Staphylococcus aureus, a series of compounds structurally analogous to natural products were synthesized. Eight SrtA inhibitors and an ICL inhibitor having higher activities than the natural products were discovered by screening the enzyme inhibitory

  在含吲哚的天然产物对白色念珠菌的异柠檬酸裂合酶（ICL）和金黄色葡萄球菌的分选酶A（SrtA）的抑制活性的指导下，合成了一系列与天然产物结构相似的化合物。通过筛选合成化合物的酶抑制活性，发现了八种具有比天然产物更高活性的SrtA抑制剂和ICL抑制剂。在发现的SrtA抑制剂中，有六种具有比对羟基巯基苯甲酸更高的活性，这表明这些化合物具有作为替代抗菌剂的巨大潜力。
• Process for preparation of tryptophols
  申请人：John Wyeth & Brother Limited

  公开号：US04062869A1

  公开（公告）日：1977-12-13

  A process for preparing tryptophol derivatives comprises reducing a 3-indolylglyoxylic acid ester or acid halide using an alkali metal borohydride in the presence of an alcohol or ether solvent. The tryptophol derivatives prepared are useful as intermediates to pharmacologically active compounds.

  一种制备色氨酸醇衍生物的过程，包括在醇或醚溶剂的存在下，使用碱金属硼氢化物还原3-吲哚基乙酸酯或酸卤化物。制备的色氨酸醇衍生物可用作制备药理活性化合物的中间体。
• Pyrazolo[3,4-c]Quinolines, Pyrazolo[3,4-c]Naphthyridines, Analogs Thereof, and Methods
  申请人：Merrill Bryon A.

  公开号：US20090069299A1

  公开（公告）日：2009-03-12

  Pyrazolo[3,4-c]quinolines, pyrazolo[4,5-c]naphthyridines, and analogs thereof, eg., 6,7,8,9-tetrahydro pyrazolo[3,4-c]quinolines, and, pharmaceutical compositions containing the compounds, intermediates, methods of making these compounds, and methods of use of these compounds as immunomodulators, for inhibiting cytokine biosynthesis in animals and in the therapeutic or prophylactic treatment of diseases by inhibiting cytokine biosynthesis are disclosed.

  本发明涉及吡唑并[3,4-c]喹啉、吡唑并[4,5-c]萘啉及其类似物，例如6,7,8,9-四氢吡唑并[3,4-c]喹啉，以及含有这些化合物的制药组合物、中间体、制备这些化合物的方法以及将这些化合物用作免疫调节剂的方法，用于抑制动物体内的细胞因子生物合成，并在治疗或预防通过抑制细胞因子生物合成引起的疾病中使用。
• Calcium Ion Channel Modulators & Uses Thereof
  申请人：Khan Nawaz Mohammed

  公开号：US20110166136A1

  公开（公告）日：2011-07-07

  Compounds of formula (1), salts and pro-drugs wherein: R1, R2, R3 and R4 are hydrogen, alkyl, hydroxyalkyl, halogen, haloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, carboxyl, hydroxyl, nitro, amino, monalkylamino, dialkylamino, acylamino, alkoxycarbonylamino, alkylsulphonyl, arylsulphonyl, alkylsulphonylamino, arylsulphonylamino, aminosulphonyl or cyano, or any two of R1 to R4 that are adjacent on the ring may together represent the moiety —O—(CH 2 ) n —O— wherein n is 1 to 3; R5 is hydrogen or alkyl; R6 is hydrogen or alkyl; and X is selected from the group consisting of: (a) groups of formula OR7 wherein R7 is hydrogen or alkyl which is optionally substituted with a substituent selected from alkylsulfonylalkyl, saturated or partially unsaturated heterocyclic, alkoxy, carboxyl, nitro, amino, monalkylamino, dialkylamino, halogen, and alkoxycarbonyl, provided that when R7 is hydrogen or ethyl, then R1, R2, R3 and R4 cannot be selected from hydrogen, halogen and alkyl; and (b) groups of formula NR8R9 wherein R8 and R9 together with the nitrogen atom to which they are attached form a saturated or partially unsaturated heterocyclic group which optionally contains at least one more heteroatom selected from nitrogen, oxygen and sulphur atoms, said saturated or partially unsaturated heterocyclic group optionally further being substituted by one or more substituents selected from alkyl, halogen, haloalkyl, alkoxy, alkoxycarbonyl, carboxyl, nitro, amino, monalkylamino, dialkylamino and hydroxyl, provided that: (i) when R8+R9+N=piperazine, and ≧1 of R1 to R4 are hydrogen, hydroxyl, nitro, amino, alkylamino, dialkylamino, alkoxycarbonylamino, halogen, alkoxy or alkyl, the nitrogen atom at the 4-position of the piperazine is not alkyl substituted, (ii) when each of R1, R2, R3, R4, R5 and R6 is hydrogen, X is not unsubstituted piperazinyl or unsubstituted morpholino, (iii) when each of R1, R2, R4, R5 and R6 is hydrogen and R3 hydrogen, bromine or hydroxyl, X is not methoxy, (iv) when each of R2 and R3 is methoxy or they together represent —O—CH 2 —O— and each of R1, R4, R5 and R6 is hydrogen, X is not unsubstituted piperidine, are Cavx channel blockers and are of use in the treatment of various conditions including pain.

  公式（1）的化合物，盐和前药，其中： R1、R2、R3和R4分别为氢、烷基、羟基烷基、卤素、卤基烷基、烷氧基、卤基烷氧基、烷氧羰基、羧基、羟基、硝基、氨基、单烷基氨基、双烷基氨基、酰胺基、烷氧羰胺基、烷基磺酰基、芳基磺酰基、烷基磺酰胺基、芳基磺酰胺基、氨基磺酰基或氰基，或者相邻的R1到R4中的任意两个可以共同表示—O—（CH2）n—O—基团，其中n为1到3； R5为氢或烷基； R6为氢或烷基； X选自以下组： （a）OR7式基团，其中R7为氢或烷基，可选地被选自烷基磺酰基烷基、饱和或部分不饱和杂环、烷氧基、羧基、硝基、氨基、单烷基氨基、双烷基氨基、卤素和烷氧羰基的取代基替换，前提是当R7为氢或乙基时，R1、R2、R3和R4不能被选择为氢、卤素和烷基； （b）NR8R9式基团，其中R8和R9与它们所连接的氮原子共同形成饱和或部分不饱和的杂环基团，该杂环基团可选择地含有至少一个来自氮、氧和硫原子的其他杂原子，所述的饱和或部分不饱和的杂环基团可选择地进一步被一个或多个取代基替换，所述取代基被选自烷基、卤素、卤基烷基、烷氧基、烷氧羰基、羧基、硝基、氨基、单烷基氨基、双烷基氨基和羟基，前提是： （i）当R8+R9+N=piperazine，且R1到R4中≧1个为氢、羟基、硝基、氨基、烷基氨基、双烷基氨基、烷氧羰胺基、卤素、烷氧基或烷基时，哌嗪的4位氮原子不被烷基取代， （ii）当R1、R2、R3、R4、R5和R6都为氢时，X不是未取代的哌嗪基或未取代的吗啡环基， （iii）当R1、R2、R4、R5和R6都为氢且R3为氢、溴或羟基时，X不是甲氧基， （iv）当R2和R3都为甲氧基或它们共同表示—O—CH2—O—，且R1、R4、R5和R6都为氢时，X不是未取代的哌啶基， 它们是Cavx通道阻滞剂，可用于治疗包括疼痛在内的各种疾病。