5-ethyl-2-trifluoroacetylamino-1,3,4-thiadiazole | 22926-50-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-ethyl-2-trifluoroacetylamino-1,3,4-thiadiazole
• 英文别名: 2-trifluoroacetamido-5-ethyl-1,3,4-thiadiazole；N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-2,2,2-trifluoro-acetamide；2-ethyl-5-trifluoroacetylamino-1,3,4-thiadiazole；N-(5-ethyl-1,3,4-thiadiazol-2-yl)-2,2,2-trifluoroacetamide
• CAS: 22926-50-7
• 化学式: C₆H₆F₃N₃OS
• 分子量: 225.194
• InChiKey: SSKDCDFUABQWLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-ethyl-2-trifluoroacetylamino-1,3,4-thiadiazole 在 劳森试剂 作用下， 以 甲苯 为溶剂， 以52%的产率得到5-ethyl-2-trifluorothioacetylamino-1,3,4-thiadiazole
  参考文献：
  名称：

  Remarkable discrepancy in the predominant structures of acyl(or thioacyl)aminothiadiazoles, acyl(or thioacyl)aminooxadiazoles and related compounds having the potential for rotational, geometrical and tautomeric isomerism

  摘要：

  X-Ray crystallographic structures of 5-ethyl-2-trifluorothioacetylamino-1,3,4-thiadiazole 2, 5-ethyl-3-p-nitrobenzyl-2-trifluorothioacetylimino-1,3,4-thiadiazoline 4 and 5-ii-propyl-2-trifluoroacetylamino-1,3,4-thiadiazole 7 proved to be monomeric or dimeric bearing intermolecular hydrogen bondings and/or an intramolecular nonbonded 1,5-type (SS)-S-... or (SO)-O-... interactions. In contrast, the X-ray crystallographic structure of 5-ethyl-2-trifluoroacetylamino-1,3,4-oxadiazole 5 was shown to be dimeric involving ordinal intra- and intermolecular hydrogen bondings without any close contact. The ab initio, computational Studies (HF/6-311G*) of the four monomeric formylamino- and thioformylaminothiadiazoles(or -oxadiazoles) and formylimino- and thioformytiminothiadiazolines(or -oxadiazolines) structures 8-11 clarified the relative structure-stability order and a remarkable discrepancy in the predominant structures of the acylamino- and thioacylaminothiadiazoles and -oxadiazoles having the potential for rotational, geometrical and tautomeric isomerism. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00080-1
• 作为产物：
  描述：

  2-氨基-5-乙基-1,3,4-噻二唑 在 三乙胺 、 三氟乙酸酐 作用下， 以 水 、 乙酸乙酯 、 甲苯 为溶剂， 以237.5g (68%)的产率得到5-ethyl-2-trifluoroacetylamino-1,3,4-thiadiazole
  参考文献：
  名称：

  Process for producing tetrazolylated biphenylmethane derivatives

  摘要：

  本发明涉及一种生产四唑基联苯甲烷衍生物(6)或其盐的方法，符合以下所述的反应方案，其中R.sup.1代表烷基；R.sup.2代表H等；Z代表卤素等；A代表环烯烃等。根据上述方法，可以通过简短的步骤工业化地和有利地生产四唑基联苯甲烷衍生物。

  公开号：

  US05912353A1

文献信息

• Process for producing N-biphenylmethylthiadiazoline derivative or salt
  申请人：Wakunaga Seiyaku Kabushiki Kaisha

  公开号：US05965738A1

  公开（公告）日：1999-10-12

  Described is a process for producing an N-biphenyl-methylthiadiazoline derivative (7) in accordance with the reaction formula described below. According to the process of the present invention, it is possible to produce a compound (7) advantageously from the industrial viewpoint. ##STR1##

  描述了根据下面描述的反应公式生产N-联苯基-甲基噻二唑啉衍生物（7）的过程。根据本发明的方法，可以从工业角度有利地生产化合物（7）。
• Biphenylmethane derivatives and pharmaceuticals containing the same
  申请人：Wakunaga Seiyaku Kabushiki Kaisha

  公开号：US05654322A1

  公开（公告）日：1997-08-05

  This invention relates to a biphenylmethane derivative represented by the formula (1): ##STR1## wherein A represents a group ##STR2## in which R.sup.1, X, Y, Z and B are as defined in the Specification. The compounds have potent angiotensin II antagonist activity and anti-hypertensive effect. They have therapeutic utility for circulatory diseases such as hypertension, heart diseases and cerebral apoplexy.

  这项发明涉及一种由式（1）表示的联苯甲烷衍生物：##STR1##其中A代表一个基团##STR2##其中R.sup.1、X、Y、Z和B如规范中定义。这些化合物具有强大的抗肾素II拮抗活性和降压作用。它们在治疗循环系统疾病如高血压、心脏病和脑卒中方面具有治疗效用。
• Antitumor activity of 5-substituted 2-acylamino-1,3,4-thiadiazoles against transplantable rodent tumors.
  作者：KENICHI MIYAMOTO、RYOZO KOSHIURA、MASAO MORI、HIDEHARU YOKOI、CHIKA MORI、TAKAAKI HASEGAWA、KICHITARO TAKATORI

  DOI：10.1248/cpb.33.5126

  日期：——

  The antitumor activities of twelve 2-N-and/or 5-substituted 2-amino-1, 3, 4-thiadiazole analogs were tested on Lewis lung carcinoma in mice by intraperitoneal administration. 2-Amino-1, 3, 4-thiadiazole (ATDA), 2-formamido-1, 3, 4-thiadiazole and 2-trifluoroacetamido-1, 3, 4-thiadiazole significantly prolonged the life span of tumor bearing mice. 5-Substituted analogs and 2-urethane and 2-carbamate type compounds were inactive. 2-Formamido-1, 3, 4-thiadiazole showed more potent activity than the parent compound ATDA against P388, L1210 leukemia, B16 melanoma and Lewis lung carcinoma. The differences in the antitumor activity among ATDA analogs are discussed.

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• Intramolecular Nonbonded S···O Interaction Recognized in (Acylimino)thiadiazoline Derivatives as Angiotensin II Receptor Antagonists and Related Compounds
  作者：Yoshimitsu Nagao、Terukage Hirata、Satoru Goto、Shigeki Sano、Akikazu Kakehi、Kinji Iizuka、Motoo Shiro

  DOI：10.1021/ja973109o

  日期：1998.4.1

  of the (acylimino)thiadiazoline derivatives (1−3) as angiotensin II receptor antagonists. The relative stability of the nonbonded 1,5-type S···O interaction was investigated using the X-ray crystallographic analyses and the ab initio MO calculations (HF/3-21G*, 6-31G*, and 6-311+G**) of the simplified model compounds (6, 7, and 9). The concept of mimic-fused bicyclic heterocycles consisting of fairly

  在（酰基亚氨基）噻二唑啉衍生物（1-3）作为血管紧张素II受体拮抗剂的晶体结构中，分子内非键合的1,5-型S…O相互作用被识别。使用 X 射线晶体学分析和 ab initio MO 计算（HF/3-21G*、6-31G* 和 6-311+）研究了非键合 1,5 型 S···O 相互作用的相对稳定性G**) 的简化模型化合物（6、7 和 9）。由相当稳定的非键合 S···O 相互作用组成的模拟稠合双环杂环的概念似乎是设计和开发各种药物的有效方法。
• BIPHENYLMETHANE DERIVATIVE AND MEDICINE CONTAINING THE SAME
  申请人：WAKUNAGA SEIYAKU KABUSHIKI KAISHA

  公开号：EP0656355A1

  公开（公告）日：1995-06-07

  A biphenylmethane derivative represented by general formula (I), a salt thereof, and a remedy for circulatory system diseases containing the same, wherein A represents the group (II) or (III) wherein R¹ represents hydrogen, lower alkyl, lower cycloalkyl, optionally substituted phenyl, optionally substituted aralkyl, optionally substituted acyl, or amino acid residue; X represents oxygen or sulfur; Y represents nitrogen or =CR²-; Z represents oxygen, nitrogen or =CR³- (excluding the case where both of Y and Z represent nitrogen simultaneously); R² and R³ represent each independently hydrogen, halogen, optionally substituted lower alkyl, optionally protected carboxyl, lower cycloalkyl, lower alkenyl, lower alkoxy, lower alkylthio or aryl, or alternatively R², R³ and the adjacent carbon atoms may be combined together to form an optionally substituted benzene ring; and B represents cyano, optionally protected carboxyl or optionally protected tetrazol-5-yl. This compound has such potent angiotensin II antagonism and hypotensive effect that it is useful for treating circulatory system diseases such as hypertension, cardiac diseases and cerebral apoplexy.

  通式(I)代表的联苯甲烷衍生物、其盐和含有该衍生物的治疗循环系统疾病的药物，其中A代表基团(II)或(III)，其中R¹代表氢、低级烷基、低级环烷基、任选取代的苯基、任选取代的芳烷基、任选取代的酰基或氨基酸残基；X代表氧或硫；Y代表氮或＝CR²-；Z 代表氧、氮或 =CR³-（不包括 Y 和 Z 同时代表氮的情况）；R² 和 R³ 各自独立地代表氢、卤素、任选取代的低级烷基、任选保护的羧基、低级环烷基、低级烯基、低级烷氧基、低级烷硫基或芳基，或者 R²、R³ 和相邻碳原子可以结合在一起形成任选取代的苯环；B 代表氰基、任选保护的羧基或任选保护的四唑-5-基。该化合物具有很强的血管紧张素 II 拮抗和降压作用，可用于治疗高血压、心脏病和脑中风等循环系统疾病。