噻吩-1-羧酸 | 96248-95-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二硫类化合物
• 中文名称: 噻吩-1-羧酸
• 英文名称: thianthren-1-ylcarboxylic acid
• 英文别名: thianthrene-1-carboxylic acid；1-thianthrenecarboxylic acid；1-thianthrencarboxylic acid；Thianthren-1-carbonsaeure；Thianthren-carbonsaeure-(1)
• CAS: 96248-95-2
• 化学式: C₁₃H₈O₂S₂
• 分子量: 260.337
• InChiKey: KBELHODUGYUEBC-UHFFFAOYSA-N

物化性质

• 熔点：
  217-218 °C
• 沸点：
  441.2±44.0 °C(Predicted)
• 密度：
  1.466±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  噻吩-1-羧酸 在 sodium ethanolate 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 54.0h， 生成 1-(thianthren-1-yl)butane-1,3-dione
  参考文献：
  名称：

  Pyranone, Thiopyranone, and Pyridone Inhibitors of Phosphatidylinositol 3-Kinase Related Kinases. Structure−Activity Relationships for DNA-Dependent Protein Kinase Inhibition, and Identification of the First Potent and Selective Inhibitor of the Ataxia Telangiectasia Mutated Kinase

  摘要：

  Structure-activity relationships have been investigated for inhibition of DNA-dependent protein kinase (DNA-PK) and ATM kinase by a series of pyran-2-ones, pyran-4-ones, thiopyran-4-ones, and pyridin-4-ones. A wide range of IC50 values were observed for pyranones and thiopyranones substituted at the 6-position, with the 3- and 5-positions proving intolerant to substitution. Related pyran-2-ones, pyran-4-ones, and thiopyran-4-ones showed similar IC50 values against DNA-PK, whereas the pyridin-4-one system proved, in general, ineffective at inhibiting DNA-PK. Extended libraries exploring the 6-position of 2-morpholino-pyran-4-ones and 2-morpholino-thiopyrano-4-ones identified the first highly potent and selective ATM inhibitor 2-morpholin-4-yl-6-thianthren-1-yl-pyran-4-one (151C; ATM; IC50 = 13 nM) and revealed constrained SARs for ATM inhibition compared with DNA-PK. One of the most potent DNA-PK inhibitors identified, 2-(4-methoxyphenyl)-6-(morpholin-4-yl)pyran-4-one (16; DNA-PK; IC50 = 220 nM) effectively sensitized HeLa cells to the topoisomerase II inhibitor etoposide in vitro.

  DOI：

  10.1021/jm061121y
• 作为产物：
  描述：

  噻蒽 在 正丁基锂 、 乙醚 、 苯 作用下， 生成 噻吩-1-羧酸
  参考文献：
  名称：

  Metalation of Thianthrene-5-dioxide by n-Butyllithium and by Phenyllithium and Cleavage of Thianthrene-5,5,10-trioxide by n-Butyllithium

  摘要：

  DOI：

  10.1021/ja01558a055

文献信息

• Potential antitumor agents. 54. Chromophore requirements for in vivo antitumor activity among the general class of linear tricyclic carboxamides
  作者：Brian D. Palmer、Gordon W. Rewcastle、Graham J. Atwell、Bruce C. Baguley、William A. Denny

  DOI：10.1021/jm00399a003

  日期：1988.4

  thioxanthenone, anthraquinone, pyridoquinazoline, dibenzodioxin, thianthrene, phenothiazine, phenoxazine, dibenzofuran, carbazole, and pyridoindole) of the general class of N-[2-(dimethylamino)ethyl] linear tricyclic carboxamides. Only the compounds containing coplanar chromophores intercalated DNA. There is an absolute requirement for an oxygen or aromatic nitrogen (possibly as hydrogen-bond acceptors) peri to

  报道了一般结构的许多不同实例（ac啶，吩嗪，蒽，a啶、,吨酮，噻吨酮，蒽醌，吡啶并喹唑啉，二苯并二恶英，噻吨，吩噻嗪，吩恶嗪，二苯并呋喃，咔唑和吡啶基吲哚的结构-抗肿瘤活性关系。 N- [2-（二甲基氨基）乙基]线性三环羧酰胺。仅包含共面发色团的化合物插入DNA。绝对需要羧酰胺周围的氧或芳族氮（可能是氢键受体），以及用于生物活性的平面环几何形状。除了进一步描述这类化合物的药效基团的性质外，该工作还确定了二苯并[1,4]二恶英是一种具有体内抗肿瘤活性的新型DNA嵌入发色团。
• ATM inhibitors
  申请人：Kudos Pharmaceuticals Ltd

  公开号：US20040002492A1

  公开（公告）日：2004-01-01

  The application concerns a compound of formula I: 1 wherein one of P and Q is O, and the other of P and Q is CH, where there is a double bond between whichever of Q and P is CH and the carbon atom bearing the R 3 group; Y is either O or S; R 1 and R 2 are independently hydrogen, an optionally substituted C 1-7 alkyl group, C 3-20 heterocyclyl group, or C 5-20 aryl group, or may together form an optionally substituted heterocyclic ring having from 4 to 8 ring atoms; R 3 is a phenyl or pyridyl group, attached by a first bridge group selected from —S—, —S(═O)—, —S(═O) 2 —, —O—, —NR N — and CR C1 R C2 — to an optionally substituted C 5-20 carboaryl group, the phenyl or pyridyl group and optionally substituted C 5-20 carboaryl group being optionally further linked by a second bridge group, so as to form an optionally substituted C 5-7 ring, the phenyl or pyridyl group being further optionally substituted.

  该应用涉及一种具有以下式I的化合物：其中P和Q中的一个是O，另一个是CH，Q和P中的CH之一之间存在双键，并且带有R3基团的碳原子；Y可以是O或S；R1和R2独立地是氢、可选择地取代的C1-7烷基、C3-20杂环基团或C5-20芳基，或者可以一起形成具有4至8个环原子的可选择地取代的杂环环；R3是苯基或吡啶基团，通过第一桥基团连接到一个可选择地取代的C5-20碳芳基团，该苯基或吡啶基团和可选择地取代的C5-20碳芳基团可以进一步通过第二桥基团连接，从而形成一个可选择地取代的C5-7环，苯基或吡啶基团可以进一步选择性地取代。
• Synthesis of 1- and 2-substituted thianthrenes
  作者：James M. Lovell、John A. Joule

  DOI：10.1039/p19960002391

  日期：——

  Lithiation of thianthrene at C-1 allows the synthesis of various 1-substituted thianthrenes for example thianthren-1-ylboronic acid and 1-tributylstannylthianthrene, which undergo palladium-catalysed couplings with aryl halides. 2-Bromothianthrene provides an entry to 2-substituted thianthrenes via lithium–halogen exchange then reaction of 2-lithiothianthrene with electrophiles including formation of the 2-boronic acid and 2-tributylstannylthianthrene which were coupled to aryl halides.

  噻蒽 C-1 的锂化反应可以合成各种 1-取代的噻蒽，例如噻蒽-1-基硼酸和 1-三丁基锡噻蒽，它们与芳基卤化物发生钯催化偶联反应。通过锂-卤素交换，2-溴噻蒽进入 2-取代噻蒽，然后 2-硫代噻蒽与亲电物反应，包括形成 2-硼酸和 2-三丁基锡噻蒽，并与芳基卤化物偶联。
• Synthesis of 4,6-disubstituted thianthrenes; X-ray crystal structures of 4,6-diphenylthianthrene and 1-tetrathiafulvalenylnaphthalene
  作者：James M. Lovell、Roy L. Beddoes、John A. Joule

  DOI：10.1016/0040-4020(96)00145-7

  日期：1996.3

  Lithiation of thianthrene 5-oxide, then trapping with chlorotrimethylsilane gave 4-mono-, 4,6-di, 4b, and 4,6,9-tri-TMS derivatives. Reduction of oxide 4b to the thianthrene followed by reaction with bromine gave 4,6-dibromothianthrene which coupled smoothly with phenylboronic acid producing 4,6-diphenylthianthrene, 5c. The crystal structures of 5c and of 4-(1-naphthalenyl)-2-(1,3-dithiol-2-ylidene)-1

  氧化噻吩5-氧化物，然后用三甲基氯硅烷捕集，得到4-单-，4,6-di，4b和4,6,9-tri-TMS衍生物。将氧化物4b还原成噻吨，然后与溴反应，得到4，6-二溴噻吨，其与苯基硼酸平滑地偶联，产生4，6-二苯基噻吨5c。测定了5c和4-（1-萘基）-2-（1，3-二硫醇-2-亚烷基）-1，3-二硫醇的晶体结构。
• [EN] PYRANONES USEFUL AS ATM INHIBITORS<br/>[FR] PYRANONES UTILES COMME INHIBITEURS DE L'ATM
  申请人：KUDOS PHARM LTD

  公开号：WO2003070726A1

  公开（公告）日：2003-08-28

  The application concerns a compound of formula I: (I) wherein one of P and Q is O, and the other of P and Q is H, where there is a double bond between whichever of Q and P is CH and the carbon atom bearing the R3 group;Y is either O or S;R1 and R2 are independently hydrogen, an optionally substituted C1-7 alkyl group, C3-20 heterocyclyl group, or C5-20 aryl group, or may together form an optionally substituted heterocyclic ring having from 4 to 8 ring atoms;R3 is a phenyl or pyridyl group, attached by a first bridge group selected from -S-, -S (=O)-, -S(=O)2-, -O-, -NRN- and CRC1RC2- to an optionally substituted C5-20 carboaryl group, the phenyl or pyridyl group and optionally substituted C5-20 carboaryl group being optionally further linked by a second bridge group, so as to form an optionally substituted C5-7 ring, the phenyl or pyridyl group being further optionally substituted.

  该应用涉及一种具有化学式I的化合物：（I）其中P和Q中的一个是O，另一个是H，在Q和P中的哪一个是CH和带有R3基团的碳原子之间存在双键；Y可以是O或S；R1和R2独立地是氢，可选的取代C1-7烷基，C3-20杂环基团或C5-20芳基团，或者可以共同形成具有4至8个环原子的可选取代杂环环；R3是连接到可选取代的C5-20碳基芳基基团的苯基或吡啶基团，该苯基或吡啶基团通过第一桥基团（选自-S-，-S（=O）-，-S（=O）2-，-O-，-NRN-和CRC1RC2-）连接，苯基或吡啶基团和可选取代的C5-20碳基芳基基团可以通过第二桥基团进一步连接，以形成可选取代的C5-7环，苯基或吡啶基团可以进一步取代。