苯2,1,3-噻重氮-5-羧酸酯 | 175204-21-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻二唑类
• 中文名称: 苯2,1,3-噻重氮-5-羧酸酯
• 中文别名: 苯并-2,1,3-噻二唑-5-羧酸甲酯
• 英文名称: methyl benzo[c][1,2,5]thiadiazole-5-carboxylate
• 英文别名: methyl benzo-2,1,3-thiadiazole-5-carboxylate；Methyl 2,1,3-benzothiadiazole-5-carboxylate
• CAS: 175204-21-4
• 化学式: C₈H₆N₂O₂S
• mdl: MFCD00173948
• 分子量: 194.214
• InChiKey: LRMFSMKHXKDUDG-UHFFFAOYSA-N

物化性质

• 熔点：
  90-92°C
• 沸点：
  292.1±13.0 °C(Predicted)
• 密度：
  1.413±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  避免与氧化物、酸、碱以及还原剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37
• 危险类别码：
  R36/37/38
• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P362,P403+P233,P501
• 危险性描述：
  H315,H319,H335
• 储存条件：
  保存方法：将物品存放在密闭、阴凉、通风干燥的地方。

反应信息

• 作为反应物：
  描述：

  苯2,1,3-噻重氮-5-羧酸酯 在 manganese(IV) oxide 、 lithium iodide 作用下， 以 吡啶 、 氯仿 为溶剂， 反应 3.5h， 生成 2,1,3-苯并噻二唑-5-甲醛
  参考文献：
  名称：

  Cytotoxic activities and metabolic studies of new combretastatin analogues

  摘要：

  A new series of combretastatin analogues with B-ring modifications were synthesized and evaluated for their cytotoxicity against one endothelial (HUVEC) and three tumor cell lines, e.g., the LoVo colon, the PC-3 prostate, and the U373 glioma cancer models. These new combretastatin analogues showed differential cytotoxic activities, cis derivatives 13 5-(2-Z-trimethoxyphenylethenyl)benzo[1,2-c]1,2,5-oxadiazole N (1)-oxide and 14 5-(2-Z-trimethoxyphenylethenyl)benzo[1,2,5]thiadiazole exhibiting interesting cytotoxicity both on endothelial and on tumor cells. Unlike the cis benzofurazan 12 5-(2-Z-trimethoxyphenylethenyl)benzo[1,2-c]1,2,5-oxadiazole, induction of apoptosis by 13 appeared to be through caspase-3 activation. Metabolic investigations showed a positive correlation between highly metabolized compounds and cytotoxic activity, suggesting that highly cytotoxic derivatives may act as pro-drug via a reductive metabolization to more active metabolites.

  DOI：

  10.1007/s00044-015-1363-3
• 作为产物：
  描述：

  3,4-二氨基苯甲酸甲酯 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 苯2,1,3-噻重氮-5-羧酸酯
  参考文献：
  名称：

  无光催化剂可见光触发苯并 [c][1,2,5] 噻二唑胺化：由 C(sp2)-H 键直接形成 C-N 键

  摘要：

  芳烃协议的光氧化还原胺化主要包括光催化剂介导的转化。在此，我们介绍了无光催化剂、可见光促进的 C(sp 2 )–H 直接转化为 C(sp 2 )–N 的方法。多用途苯并噻二唑用作模型合成子，仲胺用作胺化剂。机理研究表明，自由基反应机制是通过以氮为中心的自由基生成，然后添加芳烃进行的，这在本发明的苯并噻二唑与仲胺的胺化方案中以原子经济方式得到证明。

  DOI：

  10.1039/d2cc05811a

文献信息

• Substitution Effect on 2-(Oxazolinyl)-phenols and 1,2,5-Chalcogenadiazole<i>-</i>Annulated Derivatives: Emission-Color-Tunable, Minimalistic Excited-State Intramolecular Proton Transfer (ESIPT)-Based Luminophores
  作者：Dominik Göbel、Pascal Rusch、Daniel Duvinage、Tim Stauch、Nadja-C. Bigall、Boris J. Nachtsheim

  DOI：10.1021/acs.joc.1c00846

  日期：2021.11.5

  Minimalistic 2-(oxazolinyl)-phenols substituted with different electron-donating and -withdrawing groups as well as 1,2,5-chalcogenadiazole-annulated derivatives thereof were synthesized and investigated in regard to their emission behavior in solution as well as in the solid state. Depending on the nature of the incorporated substituent and its position, emission efficiencies were increased or diminished

  合成了被不同给电子和吸电子基团取代的简约 2-(恶唑啉基)-苯酚及其 1,2,5-硫属二唑环化衍生物，并研究了它们在溶液和固体中的发射行为状态。根据引入的取代基的性质及其位置，发射效率会增加或减少，从而产生 AIE 或 ACQ 特性。单晶分析揭示了 J 型和 H 型包装基序以及迄今为止未描述的以酮形式分离的基于 ESIPT 的荧光团。
• Dehydroamino acids
  申请人：——

  公开号：US20020161237A1

  公开（公告）日：2002-10-31

  Compounds of formula 1 and 1-1, 1 wherein R 1 is hydrogen, hydroxy, amino or halogen, R 2 is hydrogen, hydroxy, or halogen and R 3 is hydrogen (Formula 1) or R 1 is hydrogen and R 2 and R 3 taken together with the ethenylene group connecting them form phenyl, pyrrole, pyrroline, oxopyrroline, pyrazole, triazole, or imidazole (Formula 1-1), A is 2 R 4 R 5 are hydrogen, methyl, ethyl or halogen except that R 4 r 5 cannot both be hydrogen; and 1) B is hydrogen, or lower alkyl; or 2) B is 3 where R 6 R 7 R 8 and R 9 are independently hydrogen, hydroxy, aminosulfonyl, halogen, lower alkoxy, cyano, amino, lower alkyl, lower alkyl amino, or nitro; or 3) B is 4 where R 10 is hydrogen, hydroxy, halogen, or lower alkyl and C is a five- or six- membered ring with 0 to 3 heteroatoms which heteroatoms are selected from nitrogen, oxygen, and sulfur, which ring may be unsubstituted or mono- or di- substituted with lower alkyl, cycloalkyl, amino, or substituted amino; 4) B is 5 where X and Y are independently methylene or nitrogen; or 5) B is 6 where at leat one of T, U, V, or W is nitrogen, and any of T, U, V or W which is carbon may be substituted with lower alkyl, lower alkyl amino, lower alkoxy, hydroxy, aminosulfonyl, halogen, cyano, amino, or nitro; or 6) B is 7 where Y is carbon or nitrogen; or 7) B is a five-membered aromatic ring with 1 to 3 heteratoms selected from nitrogen, oxygen, and sulfur which ring may be unsubstituted or mono- or di-substituted with lower alkyl, cycloalky, trifluoroloweralkyl, amino, halogen, substituted amino, or which ring may be fused with a 5 or 6 membered aromatic ring containing 0 to 3 heteroatoms which heteroatoms are selected from nitrogen, oxygen, and sulfur; and pharmaceutically acceptable salts thereof, and related prodrugs, pharmaceutical compositions and methods of treatment, which compounds are useful for treating psoriasis.

  式1和1-1的化合物， 其中R1是氢，羟基，氨基或卤素，R2是氢，羟基或卤素，R3是氢（式1）或R1是氢，R2和R3连同连接它们的乙烯基团形成苯基，吡咯，吡咯烯，氧代吡咯烯，吡唑，三唑或咪唑（式1-1），A是 R4R5是氢，甲基，乙基或卤素，但R4R5不能同时为氢；和 1）B是氢或低碳烷基；或 2）B是 R6R7R8和R9独立地是氢，羟基，氨基磺酰基，卤素，低烷氧基，氰基，氨基，低烷基，低烷基氨基或硝基； 或3）B是 R10是氢，羟基，卤素或低碳烷基，C是具有0到3个异原子的五元或六元环，这些异原子选自氮，氧和硫，该环可以未取代或单取代或双取代为低烷基，环烷基，氨基或取代氨基； 4）B是 X和Y独立地是亚甲基或氮；或 5）B是 至少T，U，V或W中的一个是氮，任何是碳的T，U，V或W可以被低烷基，低烷基氨基，低烷氧基，羟基，氨基磺酰基，卤素，氰基，氨基或硝基取代；或 6）B是 Y是碳或氮； 或 7）B是具有1到3个异原子的氮，氧和硫中选择的五元芳香环，该环可以未取代或单取代或双取代为低烷基，环烷基，三氟低烷基，氨基，卤素，取代氨基，或该环可以与含有0到3个异原子的五元或六元芳香环融合，这些异原子选自氮，氧和硫；及其药学上可接受的盐，相关的前药，药物组合物和治疗方法，这些化合物对治疗牛皮癣有用。
• Benzofurazan compounds which enhance AMPA receptor activity
  申请人：The Regents of the University of California

  公开号：US06313115B1

  公开（公告）日：2001-11-06

  Compounds of general structural formula (I) are shown to have AMPA receptor enhancing properties. The compounds are useful for such therapeutic purposes as facilitating the learning of behaviors dependent upon AMPA receptors, and in treating conditions, such as memory impairment, in which AMPA receptors, or synapses utilizing these receptors, are reduced in numbers or efficiency. They may also be used to enhance excitatory synaptic activity in order to restore an imbalance between brain subregions, as in treatment of schizophrenia or schizophreniform behavior.

  一般结构式（I）的化合物被证明具有增强AMPA受体的特性。这些化合物可用于促进依赖于AMPA受体的行为学习等治疗目的，并用于治疗记忆障碍等情况，其中AMPA受体或利用这些受体的突触数量或效率降低。它们也可以用于增强兴奋性突触活动，以恢复大脑亚区之间的不平衡，如治疗精神分裂症或类精神分裂行为。
• Benzofurazan compounds for enhancing glutamatergic synaptic responses
  申请人：The Regents of the University of California

  公开号：US06110935A1

  公开（公告）日：2000-08-29

  Compounds of the general structural formula ##STR1## are shown to have AMPA receptor enhancing properties. The compounds are useful for such therapeutic purposes as facilitating the learning of behaviors dependent upon AMPA receptors, and in treating conditions, such as memory impairment, in which AMPA receptors, or synapses utilizing these receptors, are reduced in numbers or efficiency. They may also be used to enhance excitatory synaptic activity in order to restore an imbalance between brain subregions, as in treatment of schizophrenia or schizophreniform behavior.

  具有一般结构式##STR1##的化合物已被证明具有AMPA受体增强性质。这些化合物可用于促进依赖于AMPA受体的行为学习，以及治疗AMPA受体或利用这些受体的突触数量或效率降低的记忆障碍等情况。它们还可以用于增强兴奋性突触活动，以恢复大脑亚区之间的不平衡，如治疗精神分裂症或分裂症行为。
• [EN] BENZOFURAZAN COMPOUNDS WHICH ENHANCE AMPA RECEPTOR ACTIVITY<br/>[FR] COMPOSES A BASE DE BENZOFURAZAN RENFORÇANT L'ACTIVITE DU RECEPTEUR DE L'AMPA
  申请人：CORTEX PHARMACEUTICALS, INC.

  公开号：WO1998035950A1

  公开（公告）日：1998-08-20

  (EN) Compounds of general structural formula (I) are shown to have AMPA receptor enhancing properties. The compounds are useful for such therapeutic purposes as facilitating the learning of behaviors dependent upon AMPA receptors, and in treating conditions, such as memory impairment, in which AMPA receptors, or synapses utilizing these receptors, are reduced in numbers or efficiency. They may also be used to enhance excitatory synaptic activity in order to restore an imbalance between brain subregions, as in treatment of schizophrenia or schizophreniform behavior.(FR) La présente invention concerne des composés représentés par la formule structurelle générale (I) et qui font preuve d'une aptitude à renforcer l'activité du récepteur AMPA. Ces composés conviennent à des fins thérapeutiques et notamment pour l'apprentissage de comportements liés aux récepteurs de l'AMPA, et pour le traitement d'états tels que les déficiences de la mémoire dans lesquelles les récepteurs de l'AMPA, ou les synapses utilisant ces récepteurs, sont présents en nombre réduit ou font preuve d'une moindre efficacité. Ces composés permettent également d'augmenter l'activité excitatrice des synapses afin de rétablir un équilibre entre les sous-régions du cerveau, comme dans le cas du traitement de la schizophrénie ou des comportements schizophréniformes.

  (中) 通用结构式（I）的化合物被证明具有增强AMPA受体的性质。这些化合物可用于促进依赖于AMPA受体的行为的学习，以及治疗AMP受体数量或效率降低的病症，例如记忆障碍。它们还可以用于增强兴奋性突触活动，以恢复大脑亚区之间的平衡，例如治疗精神分裂症或类精神分裂行为。