2-(苯甲酰基氨基硫代氨基)苯甲酸 | 13277-24-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(苯甲酰基氨基硫代氨基)苯甲酸
• 英文名称: 2-(3-benzoylthioureido)benzoic acid
• 英文别名: 2-(Benzoylcarbamothioylamino)benzoic acid
• CAS: 13277-24-2
• 化学式: C₁₅H₁₂N₂O₃S
• mdl: MFCD03242060
• 分子量: 300.338
• InChiKey: ZFFHSAGSCWUIBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  111
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  2-(苯甲酰基氨基硫代氨基)苯甲酸 在 吡啶 、 硫酸 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 tert-butyl (4-oxo-4H-3,1-benzothiazin-2-ylcarbamoyl)-benzylcarbamate
  参考文献：
  名称：

  苯并噻嗪酮：结构上与黄嘌呤和腺嘌呤衍生物无关的新型腺苷受体拮抗剂

  摘要：

  2-（酰基）氨基-4 H -3,1-苯并噻嗪-4-酮和相关的噻吩并噻嗪酮被认为是腺苷受体（ARs）上结构上新颖的拮抗剂。发现6-甲基-2-苯甲酰氨基-4 H -3,1-苯并噻嗪-4-酮（10d）是一种平衡的AR拮抗剂，对所有人类（h）亚型均具有亲和力（K i hA 1 65.6 nM; hA 2A 120 nM； hA 2B 360 nM； hA 3 30.4 nM），而在大鼠（r）中，10d是一种高效的A 1选择性拮抗剂（rA 1 7.7 nM； rA 2A 546 nM； rA 2B 679 nM，rA 3> 10000 nM）。发现2-（4-甲基苯甲酰氨基）-4 H -3,1-苯并噻嗪-4-酮（10 g）是对人A 2A（68.8 nM）和A 3 AR（23.0 nM）的有效拮抗剂，相对于其他人类AR亚型。与A 1和A 3 AR相比，A 2A和A 2B AR可以容忍庞大的2-酰基取代基。叔丁基（4-oxo-4

  DOI：

  10.1021/jm300029s
• 作为产物：
  描述：

  N-(4-oxo-4H-benzo[d][1,3]thiazin-2-yl)benzamide 在 3-(cyclohexylamino)propanesulfonic acid buffer 、 水 作用下， 以 乙腈 为溶剂， 生成 2-(苯甲酰基氨基硫代氨基)苯甲酸
  参考文献：
  名称：

  3,1-Benzothiazin-4-ones and 3,1-Benzoxazin-4-ones: Highly Different Activities in Chymotrypsin Inactivation

  摘要：

  3,1-Benzothiazin-4-ones are suIfur analogs of the potent serine protease inactivators of the 3, l-benzoxazin-4-one type, which acylate the serine residue within the active site of the enzymes. A series of 2-amino-3,1-benzothiazinones was synthesized, but these compounds showed only very little inhibitory activity toward chymotrypsin, a model serine protease. Detailed investigations revealed that benzothiazinones and benzoxazinones react with identical mechanisms, but benzothiazinones acylate chymotrypsin with much lower rate constants. Investigations of nonenzymatic hydrolysis showed the benzothiazinones to be intrinsically more stable than benzoxazinones. It was concluded from spectroscopic results, that benzoxazinones are highly activated due to the absence of ester-like resonance. 2-Benzoylamino-4H-3,1-benzoxazin-4-one was found to be a new, highly active chymotrypsin inactivator. In contrast, benzothiazinones were found to be resonance stabilized. The contribution of a resonance structure with an exocyclic oxanion to the overall structure of the benzothiazinones and its nonproductive binding to the active site explained their low reactivity toward chymotrypsin. (C) 1995 Academic Press, Inc.

  DOI：

  10.1006/bioo.1995.1006

文献信息

• P(III)‐Mediated Cascade C‐N/C‐S Bond Formation: A Protocol towards the Synthesis of <i>N</i> , <i>S</i> ‐Heterocycles and Spiro Compounds
  作者：Saibabu Polina、V. P. Rama Kishore Putta、Raghuram Gujjarappa、Virender Singh、Prasad Pralhad Pujar、Chandi C. Malakar

  DOI：10.1002/adsc.202001149

  日期：2021.1.19

  of C−N/C−S bond has been devised. The developed heterocyclization method was exercised for the synthesis of a diverse range of N,S‐heterocycles and related spiro molecules. P(NMe2)3 revealed the maximum efficacies under the aerobic reaction conditions and a spectrum of bis‐nucleophiles, and isothiocyanates were tolerated well to serve the access of manifold immense molecules.

  已经设计了AP（III）介导的C-N / C-S键的构建方法。运用发达的杂环化方法合成了各种N，S杂环和相关螺环分子。P（NMe 2）3显示了在有氧反应条件下和双亲核试剂谱中的最大效率，并且异硫氰酸酯具有良好的耐受性，可用于吸收大量巨大的分子。
• Zeolite: An efficient catalyst for the synthesis of various heterocyclic compounds
  作者：R. Sreekumar、P. Rugmini、Raghavakaimal Padmakumar

  DOI：10.1016/s0040-4039(97)00606-0

  日期：1997.5

  A novel heterogeneous catalytic method to synthesize various heterocyclic compounds of biological interest, aminobenzisothiazole [2a-h] and 1,3-thiazine derivatives [4, 6], using an environmentally attractive solid catalyst, zeolite, is described.

  描述了一种新颖的非均相催化方法，该方法使用对环境有吸引力的固体催化剂沸石来合成各种具有生物意义的杂环化合物，氨基苯并噻唑[ 2a-h]和1,3-噻嗪衍生物[4，6]。
• Mehrcyclische Azine mit Heteroatomen in 1- und 3-Stellung, 25. Mitt.: 2-Amino-4-oxo-4H-3,1-benzothiazine: Darstellung,Dimroth-Umlagerung zu 4-Oxo-2-thioxo-1,2,3,4-tetrahydrochinazolinen und MS/MS-Fragmentierung
  作者：Siegfried Leistner、Michael Gütschow、Joachim Stach

  DOI：10.1002/ardp.19903231009

  日期：——

  2‐Amino‐4‐oxo‐4H‐3,1‐benzothiazinen 4a–c. Entgegen Literaturangaben geben 1 oder 2 unter anderen Reaktionsbedingungen durch Cyclokondensation die 2‐Benzoylamino‐4‐oxo‐4H‐3,1‐benzothiazine 6a–c. Dimroth‐Umlagerung von 4 führt zu den 2‐Thioxochinazolinen 5. Die ms Fragmentierung von 4, 5 und 6 wird diskutiert.

  苯甲酰硫脲衍生物 1-3 与浓反应。H2SO4 到 2-amino-4-oxo-4H-3,1-benzothiazines 4a – c。与文献相反，1 或 2 在不同反应条件下通过环缩合反应得到 2-苯甲酰氨基-4-氧代-4H-3,1-苯并噻嗪 6a-c。4 的 Dimroth 重排导致 2- thioxoquinazolines 5。讨论了 4、5 和 6 的 ms 碎裂。
• SYNTHESIS AND BIOLOGICAL ACTIVITY OF<i>N</i>-AROYL-<i>N</i>′-SUBSTITUTED THIOUREA DERIVATIVES
  作者：You-Ming Zhang、Tai-Bao Wei、Li-Ming Gao

  DOI：10.1081/scc-100105882

  日期：2001.1

  A series of N-aroyl-N ' -substituted thiourea derivatives have been prepared in good to excellent yields under the condition of solid-liquid phase transfer catalysis using polyethylene glycol-400(PEG-400) as the catalyst. The products have been characterized on the basis of analytical and spectral (IR and H-1 NMR) data. The promoting effects of some compounds on wheat growth have been tested preliminary.
• Dual Targeting of Adenosine A_2A Receptors and Monoamine Oxidase B by 4<i>H</i>-3,1-Benzothiazin-4-ones
  作者：Anne Stößel、Miriam Schlenk、Sonja Hinz、Petra Küppers、Jag Heer、Michael Gütschow、Christa E. Müller

  DOI：10.1021/jm400336x

  日期：2013.6.13

  Blockade of A(2A) adenosine receptors (A(2A)ARs) and inhibition of monoamine oxidase B (MAO-B) in the brain are considered attractive strategies for the treatment of neurodegenerative diseases such as Parkinson's disease (PD). In the present study, benzothiazinones, e.g., 2-(3-chlorophenoxy)-N-(4-oxo-4H-3,1-benzothiazin-2-yl)acetamide (13), were identified as a novel class of potent MAO-B inhibitors (IC50 human MAO-B: 1.63 nM). Benzothiazinones with large substituents in the 2-position, e.g., methoxycinnamoylamino, phenylbutyrylamino, or chlorobenzylpiperazinylbenzamido residues (14, 17, 27, and 28), showed high affinity and selectivity for A(2A)ARs (K-i human A(2A)AR: 39.5-69.5 nM). By optimizing benzothiazinones for both targets, the first potent, dual-acting A(2A)AR/MAO-B inhibitors with a nonxanthine structure were developed. The best derivative was N-(4-oxo-4H-3,1-benzothiazin-2-yl)-4-phenylbutanamide (17, K-i human A(2A), 39.5 nM; IC50 human MAO-B, 34.9 nM; selective versus other AR subtypes and MAO-A), which inhibited A(2A)AR-induced cAMP accumulation and showed competitive, reversible MAO-B inhibition. The new compounds may be useful tools for validating the A(2A)AR/MAO-B dual target approach in PD.